178 Topics in Current Chemistry: Small Ring Compounds in Organic Synthesis V

163 Pages·1996·7.3 MB·English

by  Armin de Meijere, A. Brandi, F.M. Cordero, A. Goti, T. Hirao

7 8 Topicsi n Current Chemistry
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Small Ring Compounds
in Organic Synthesis V
Volume Editor: A. de Meijere
With contributions by
A. Brandi, F. M. Cordero,
A. Goti, T. Hirao
With 5 Figures and 48 Tables
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Volume Editor
Prof. Dr. Armin de Meijere
Georg-August-Universit/it G6ttingen
Institut ftir Organische Chemie
TammannstraBe 2
D-37077 G6ttingen, FRG
Editorial Board
Prof. Dr. Jack D. Dunitz Laboratorium for Organische Chemie
der Eidgen6ssischen Hochschule
Universit~RsstraBe 6/8, CH-8006 Ziirich
Prof. Dr. Klaus Hafner Institut for Organische Chemie der TH,
PetersenstraBe 15, 64287 Darmstadt, FRG
Prof. Dr. Kendal N. Honk University of California, Department
of Chemistry and Biochemistry, 405 Hilgard Avenue,
Los Angeles, CA 90024-1589, USA
Prof. Dr. Sho ho Faculty of Pharmaceutical Sciences,
Tokushima Bunri University,
Tokushima 770, Japan
Prof. Dr. Jean-Marie Lehn Institut de Chimie, Universit, ~ de Strasbourg,
1 rue Blaise Pascal, B. P. Z 296/R8, F-67008 Strasbourg-Cedex
Prof. Dr. Kenneth N. Raymond Department of Chemistry, University of California,
Berkeley, CA 94720, USA
Prof. Dr. Charles tE Rees Hofmann Professor of Organic Chemistry, Department
of Chemistry, Imperial College of Science and Technology,
South Kensington, London SW7 2AY, England
Prof. Dr. Joachim Thiem Institut fOr Organische Chemie, Universitit Hamburg,
Martin-Luther-King-Platz 6, 20146 Hamburg, FRG
Prof. Dr. Fritz VOgtle Institut fOr Organische Chemie and Biochemie der Universit~it,
Gerhard-Domagk-StruBe 1, 53121 Bonn, FRG
Table of Contents
Cycioadditions Onto Methylene- and A l k y l i d e n e -
c y c l o p r o p a n e Derivatives
A. Goti, F. M. Cordero , A. Brandi . . . . . . . . . . . . , . . . . . . . . . .
Selective Transformations of Small Ring
Compounds in Redox Reactions
T. Hirao . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 99
A u t h o r I n d e x V o l u m e s 151 - 178 . . . . . . . . . . . . . . . . . . . . . . . . 149
Table of Contents of Volume 155
Small Ring Compounds in Organic Synthesis IV
Metal Homoenolates from Siloxyclopropranes
I. Kuwajima and E. Nakamura
Gem-Dihalocyclopropanes in Organic Synthesis
R. R. Kostikov, A. P. Molchanov and H. Hopf
Through-Bond Modulation of Reaction Centers by Remote
Substituents
T.-L. Ho
Preface
Ten years have passed since the first volume on "Small Ring Compounds in Organic
Synthesis" was published within the series Topics in Current Chemistry (Vol. 133),
and three more volumes have appeared in the meantime (Vol. 135, 144, t55).
Wouldn't that be enough?
Although this collection of reviews by individual authors, who are themselves
actively engaged in research with the use of small ring compounds in Organic
Synthesis, has not been and is not intended to be comprehensive, the field is
developing at such a rate that coverage of new topics appears highly appropriate.
The importance of small ring chemistry can be estimated from the fact that a
forthcoming volume of Houben-Weyl "Methods of Organic Chemistry" on three-
and four-membered carbocyclic compounds only covering the literature of the last
25 years will comprise over 5000 pages. Extraordinary new natural products have
been discovered which contain fatty acid analogues with four and even five adjecent
cyclopropyl groups. Just to name a single type of cyclopropane derivative, a recent
survey has uncovered 91 pharmaceutically important compounds which contain a
cyclopropylamine substructure. Clearly, the answer to the above question is "No".
The two articles in this current volume describe recent developments with small
ring compounds which have not been compiled in such a context before. T. Hirao
discusses selective transformations initiated by transition derivatives in the
construction of functionally substituted five-, six- and seven-membered rings as
well as open-chair compounds. Cycloadditions onto methylene- and alkylidene-
cyclopropane derivatives, described by A. Goti, F. M. Cordero and A. Brandi, not
only yield products with spirocyclopropane moieties which can be desirable as such
or as potential mimics of gem-dimethyl groupings, but also intermediates which
can undergo further transformations with ring-opening of the cyclopropane units.
The authors, the editor and the publisher of this and a few more forthcoming
Topics on "Small Ring Compounds in Organic Synthesis" intend to provide a service
to the research community and hope that these books will generate more and fresh
interest in this fascinating chemistry.
GSttingen, February 1996 Armin de Meijere
Cycloadditions onto Methylene- and
Aikylideneeyeiopropane Derivatives
Andrea Goti, Franca M. Cordero and Alberto Brandi
Dipartimento di Chimica Organica "U. SchilT' and Centro di Studio sulla Chimica e la Struttura dei
Composti Eterociclici e loro Applicazioni - C.N.R., Universitfi degli Studi di Firenze, via G.
Capponi 9, 1-50121-Firenze, Italy
Table of Contents
List of Symbols and Abbreviations . . . . . . . . . . . . . . . . . . . . . . . 2
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
2 Six-Membered Ring . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
2.1 D i e l s - A l d e r R e a c t i o n s . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
2.1.1 A l k y l i d e n e c y c l o p r o p a n e s as D i e n o p h i l e s . . . . . . . . . . . . 4
2.1.2 A l k y l i d e n e c y c l o p r o p a n e s as D i e n e s . . . . . . . . . . . . . . . 20
2.2 H e t e r o D i e l s - A l d e r . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26
2.2.1 A l k y l i d e n e c y c l o p r o p a n e s as D i e n o p h i l e s . . . . . . . . . . . . 26
2.2.2 A l k y l i d e n e c y c l o p r o p a n e s as D i e n e s . . . . . . . . . . . . . . . 27
2.3 I n t r a m o l e c u l a r C y c l o a d d i t i o n s . . . . . . . . . . . . . . . . . . . . . 30
3 Five-Membered Ring . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 34
3.1 1 ,3 -Dipo la r C y c l o a d d i t i o n s . . . . . . . . . . . . . . . . . . . . . . . 34
3.1.1 Azides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35
3.1.2 D i a z o a l k a n e s . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36
3.1.3 N i t r o n e s . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 38
3.1.4 O z o n e . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
3.1.5 N i t r i l e O x i d e s . . . . . . . . . . . . . . . . . . . . . . . . . . . . 50
3.1.6 N i t r i l e Yl ides . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55
3.2 [4 + 1] C y c l o a d d i t i o n s . . . . . . . . . . . . . . . . . . . . . . . . . . 56
3.3 P a u s o n - K h a n d R e a c t i o n s . . . . . . . . . . . . . . . . . . . . . . . . 58
Topics in Current Chemistry, VoL 178
~) Springer-VerlagB erlin Heidelberg 1996
A. Goti et al.
3.3.1 In termolecular P a u s o n - K h a n d Reactions . . . . . . . . . . . . 58
3.3.2 In t ramolecular P a u s o n - K h a n d Reactions . . . . . . . . . . . . 60
4 Four-Membered Ring . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 62
4.1 [2 + 2] Cycloaddi t ions to C = C Bonds . . . . . . . . . . . . . . . . 62
4.1.1 Cyclodimerizat ion . . . . . . . . . . . . . . . . . . . . . . . . . 62
4.1.2 Codimer iza t ion . . . . . . . . . . . . . . . . . . . . . . . . . . . 70
4.2 1-2 + 2] Cycloaddi t ions to C - C Bonds . . . . . . . . . . . . . . . . 83
4.3 1-2 + 2] Cycloaddi t ions to C = X Bonds . . . . . . . . . . . . . . . . 84
4.4 I-2 + 2] Cycloaddi t ions to X = Y Bonds . . . . . . . . . . . . . . . . 85
5 Three-Membered Ring . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86
5.1 Carbene (or Carbenoid) Addit ions . . . . . . . . . . . . . . . . . . . 86
5.2 Heteroa tom Addit ions . . . . . . . . . . . . . . . . . . . . . . . . . . 90
6 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 92
List of Symbols and Abbreviations
BCP Bicyclopropylidene
C O D Cyclooctadiene
CSI Chlorosulfonyl isocyanate
M C P Methylenecyclopropane
M C P B A rn-Chloroperbenzoic acid
N M O N-Methy lmorpho l ine N-oxide
P K R Pauson K h a n d Reactions
P T A D 4-Ph-1, 2, 4,-triazoline-3, 5-dione
SET Single electron transfer
T C N E Tetracyanoethylene
T M A N O Tr imethylamine N-oxide
T M M Tr imethylenemethane
Alkylidenecyclopropanesa re a peculiar class of olefinic compounds characterized by a high ring
strain, but at the same time a sufficients tability to permit their use in organic synthesis. The strain
associated with the structure of these compounds is in general responsible for the good reactivity of
the carbon-carbon double bond, even in sterically encumbered substrates. The key role of these
compounds in organic synthesis resides in the exclusive,a nd by far the most useful,p ossibility of the
introduction of a cyclopropyl ring in a more complex molecule through reactions onto the exocyclic
double bond. For this reason the investigations on the synthesis and reactivity of these compounds
has exploded in the last decade. This article wilt deal with all the reactions which involve the
exocyclic double bond of alkylidenecyclopropanes in cycloaddition processes. Albeit most of the
reactions are true pericyclic cycloaddition processes, also those reactions which lead to cycles by
stepwise processes will be reported with comments on the mechanism.