ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFOXIMINE-ACTIVATED TRIENES

D  CRAIG; N J  GEACH; C J  PEARSON; A M Z  SLAWIN; A J P  WHITE; D J  WILLIAMS

ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFOXIMINE-ACTIVATED TRIENES

D CRAIG, N J GEACH, C J PEARSON, A M Z SLAWIN, A J P WHITE, D J WILLIAMS

Research output: Contribution to journal › Article › peer-review

Abstract

A series of N-substituted sulfoximidoyl-1,6,8-nonatrienes and 1,7,9-decatrienes were synthesised and subjected to thermal intramolecular Diels-Alder (IMDA) reactions to give diastereomeric mixtures of substituted bicyclo[4.3.0]nonanes and -[4.4.0]decanes. The reactions showed varying selectivities. Endo/exo selectivity was interpreted in terms of a combination of steric factors and the asynchronous nature of the cycloadditions. Diastereofacial selectivity could be rationalised by considering attack by the diene on the less hindered face of the conformationally extended vinylic sulfoximine dienophile.

Original language	English
Pages (from-to)	6071-6098
Number of pages	28
Journal	Tetrahedron
Volume	51
Issue number	21
Publication status	Published - 22 May 1995

Keywords

NUCLEOPHILIC EPOXIDATION
ABSOLUTE-CONFIGURATION
STEREOCHEMICAL ASPECTS
ALPHA
ALDEHYDES
METHYL

Cite this

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title = "ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFOXIMINE-ACTIVATED TRIENES",

abstract = "A series of N-substituted sulfoximidoyl-1,6,8-nonatrienes and 1,7,9-decatrienes were synthesised and subjected to thermal intramolecular Diels-Alder (IMDA) reactions to give diastereomeric mixtures of substituted bicyclo[4.3.0]nonanes and -[4.4.0]decanes. The reactions showed varying selectivities. Endo/exo selectivity was interpreted in terms of a combination of steric factors and the asynchronous nature of the cycloadditions. Diastereofacial selectivity could be rationalised by considering attack by the diene on the less hindered face of the conformationally extended vinylic sulfoximine dienophile.",

keywords = "NUCLEOPHILIC EPOXIDATION, ABSOLUTE-CONFIGURATION, STEREOCHEMICAL ASPECTS, ALPHA, ALDEHYDES, METHYL",

author = "D CRAIG and GEACH, \{N J\} and PEARSON, \{C J\} and SLAWIN, \{A M Z\} and WHITE, \{A J P\} and WILLIAMS, \{D J\}",

year = "1995",

month = may,

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language = "English",

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pages = "6071--6098",

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T1 - ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFOXIMINE-ACTIVATED TRIENES

AU - CRAIG, D

AU - GEACH, N J

AU - PEARSON, C J

AU - SLAWIN, A M Z

AU - WHITE, A J P

AU - WILLIAMS, D J

PY - 1995/5/22

Y1 - 1995/5/22

N2 - A series of N-substituted sulfoximidoyl-1,6,8-nonatrienes and 1,7,9-decatrienes were synthesised and subjected to thermal intramolecular Diels-Alder (IMDA) reactions to give diastereomeric mixtures of substituted bicyclo[4.3.0]nonanes and -[4.4.0]decanes. The reactions showed varying selectivities. Endo/exo selectivity was interpreted in terms of a combination of steric factors and the asynchronous nature of the cycloadditions. Diastereofacial selectivity could be rationalised by considering attack by the diene on the less hindered face of the conformationally extended vinylic sulfoximine dienophile.

AB - A series of N-substituted sulfoximidoyl-1,6,8-nonatrienes and 1,7,9-decatrienes were synthesised and subjected to thermal intramolecular Diels-Alder (IMDA) reactions to give diastereomeric mixtures of substituted bicyclo[4.3.0]nonanes and -[4.4.0]decanes. The reactions showed varying selectivities. Endo/exo selectivity was interpreted in terms of a combination of steric factors and the asynchronous nature of the cycloadditions. Diastereofacial selectivity could be rationalised by considering attack by the diene on the less hindered face of the conformationally extended vinylic sulfoximine dienophile.

KW - NUCLEOPHILIC EPOXIDATION

KW - ABSOLUTE-CONFIGURATION

KW - STEREOCHEMICAL ASPECTS

KW - ALPHA

KW - ALDEHYDES

KW - METHYL

UR - https://www.scopus.com/pages/publications/0029070308

M3 - Article

SN - 0040-4020

VL - 51

SP - 6071

EP - 6098

JO - Tetrahedron

JF - Tetrahedron

IS - 21

ER -

ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFOXIMINE-ACTIVATED TRIENES

Abstract

Keywords

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