INTRAMOLECULAR DIELS-ALDER REACTIONS OF INTERNALLY-SUBSTITUTED TRIENYLSULFONES - SYNTHESIS OF BICYCLO[4.3.0] AND BICYCLO[4,4.0] SYSTEMS POSSESSING A BRIDGEHEAD SULFONYL GROUP

M C  CLASBY; D  CRAIG; A M Z  SLAWIN; A J P  WHITE; D J  WILLIAMS

INTRAMOLECULAR DIELS-ALDER REACTIONS OF INTERNALLY-SUBSTITUTED TRIENYLSULFONES - SYNTHESIS OF BICYCLO[4.3.0] AND BICYCLO[4,4.0] SYSTEMS POSSESSING A BRIDGEHEAD SULFONYL GROUP

M C CLASBY, D CRAIG, A M Z SLAWIN, A J P WHITE, D J WILLIAMS

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

Abstract

A series of trienes possessing internally-activated vinylic sulfone dienophilic groups undergo intramolecular Diels-Alder (IMDA) reaction with high or complete selectivity for the cis-fused products. Incorporation of silyloxy groups within the carbon tether linking the diene and dienophile results in increased IMDA reactivity. The stereochemical outcomes of these processes are rationalised in terms of the preference for an exooriented phenylsulfonyl group, and a minimisation of non-bonded interactions between the silyloxy and sulfone substituents.

Original language	English
Pages (from-to)	1509-1532
Number of pages	24
Journal	Tetrahedron
Volume	51
Issue number	5
Publication status	Published - 30 Jan 1995

Keywords

STEREOSELECTIVE SYNTHESIS
VINYLIC SULFONES
TRIENES
CYCLOADDITIONS

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title = "INTRAMOLECULAR DIELS-ALDER REACTIONS OF INTERNALLY-SUBSTITUTED TRIENYLSULFONES - SYNTHESIS OF BICYCLO[4.3.0] AND BICYCLO[4,4.0] SYSTEMS POSSESSING A BRIDGEHEAD SULFONYL GROUP",

abstract = "A series of trienes possessing internally-activated vinylic sulfone dienophilic groups undergo intramolecular Diels-Alder (IMDA) reaction with high or complete selectivity for the cis-fused products. Incorporation of silyloxy groups within the carbon tether linking the diene and dienophile results in increased IMDA reactivity. The stereochemical outcomes of these processes are rationalised in terms of the preference for an exooriented phenylsulfonyl group, and a minimisation of non-bonded interactions between the silyloxy and sulfone substituents.",

keywords = "STEREOSELECTIVE SYNTHESIS, VINYLIC SULFONES, TRIENES, CYCLOADDITIONS",

author = "CLASBY, {M C} and D CRAIG and SLAWIN, {A M Z} and WHITE, {A J P} and WILLIAMS, {D J}",

year = "1995",

month = jan,

day = "30",

language = "English",

volume = "51",

pages = "1509--1532",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "5",

}

TY - JOUR

T1 - INTRAMOLECULAR DIELS-ALDER REACTIONS OF INTERNALLY-SUBSTITUTED TRIENYLSULFONES - SYNTHESIS OF BICYCLO[4.3.0] AND BICYCLO[4,4.0] SYSTEMS POSSESSING A BRIDGEHEAD SULFONYL GROUP

AU - CLASBY, M C

AU - CRAIG, D

AU - SLAWIN, A M Z

AU - WHITE, A J P

AU - WILLIAMS, D J

PY - 1995/1/30

Y1 - 1995/1/30

N2 - A series of trienes possessing internally-activated vinylic sulfone dienophilic groups undergo intramolecular Diels-Alder (IMDA) reaction with high or complete selectivity for the cis-fused products. Incorporation of silyloxy groups within the carbon tether linking the diene and dienophile results in increased IMDA reactivity. The stereochemical outcomes of these processes are rationalised in terms of the preference for an exooriented phenylsulfonyl group, and a minimisation of non-bonded interactions between the silyloxy and sulfone substituents.

AB - A series of trienes possessing internally-activated vinylic sulfone dienophilic groups undergo intramolecular Diels-Alder (IMDA) reaction with high or complete selectivity for the cis-fused products. Incorporation of silyloxy groups within the carbon tether linking the diene and dienophile results in increased IMDA reactivity. The stereochemical outcomes of these processes are rationalised in terms of the preference for an exooriented phenylsulfonyl group, and a minimisation of non-bonded interactions between the silyloxy and sulfone substituents.

KW - STEREOSELECTIVE SYNTHESIS

KW - VINYLIC SULFONES

KW - TRIENES

KW - CYCLOADDITIONS

M3 - Article

SN - 0040-4020

VL - 51

SP - 1509

EP - 1532

JO - Tetrahedron

JF - Tetrahedron

IS - 5

ER -

INTRAMOLECULAR DIELS-ALDER REACTIONS OF INTERNALLY-SUBSTITUTED TRIENYLSULFONES - SYNTHESIS OF BICYCLO[4.3.0] AND BICYCLO[4,4.0] SYSTEMS POSSESSING A BRIDGEHEAD SULFONYL GROUP

Abstract

Keywords

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