INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL-TETHERED TRIENES

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

INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL-TETHERED TRIENES

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

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

Abstract

The synthesis and intramolecular Diels-Alder reactions of a series of silyl acetal-tethered trienes 4-9 are described. The cycloadditions show complete regioselectivity, and in all but one case give exclusively cis-fused bicyclic products. The selectivities are rationalised in terms of stereoelectronic and steric effects.

Original language	English
Pages (from-to)	11601-11622
Number of pages	22
Journal	Tetrahedron
Volume	51
Issue number	42
Publication status	Published - 16 Oct 1995

Keywords

POLAR TRANSITION-STATE
CYCLO-ADDITIONS
CYCLOADDITIONS
DIENOPHILE
1,2,4-TRIAZINES
SUBSTITUENTS
SELECTIVITY
PYRIDINES
DIENES
ETHER

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title = "INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL-TETHERED TRIENES",

abstract = "The synthesis and intramolecular Diels-Alder reactions of a series of silyl acetal-tethered trienes 4-9 are described. The cycloadditions show complete regioselectivity, and in all but one case give exclusively cis-fused bicyclic products. The selectivities are rationalised in terms of stereoelectronic and steric effects.",

keywords = "POLAR TRANSITION-STATE, CYCLO-ADDITIONS, CYCLOADDITIONS, DIENOPHILE, 1,2,4-TRIAZINES, SUBSTITUENTS, SELECTIVITY, PYRIDINES, DIENES, ETHER",

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

year = "1995",

month = oct,

day = "16",

language = "English",

volume = "51",

pages = "11601--11622",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "42",

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TY - JOUR

T1 - INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL-TETHERED TRIENES

AU - AINSWORTH, P J

AU - CRAIG, D

AU - READER, J C

AU - SLAWIN, A M Z

AU - WHITE, A J P

AU - WILLIAMS, D J

PY - 1995/10/16

Y1 - 1995/10/16

N2 - The synthesis and intramolecular Diels-Alder reactions of a series of silyl acetal-tethered trienes 4-9 are described. The cycloadditions show complete regioselectivity, and in all but one case give exclusively cis-fused bicyclic products. The selectivities are rationalised in terms of stereoelectronic and steric effects.

AB - The synthesis and intramolecular Diels-Alder reactions of a series of silyl acetal-tethered trienes 4-9 are described. The cycloadditions show complete regioselectivity, and in all but one case give exclusively cis-fused bicyclic products. The selectivities are rationalised in terms of stereoelectronic and steric effects.

KW - POLAR TRANSITION-STATE

KW - CYCLO-ADDITIONS

KW - CYCLOADDITIONS

KW - DIENOPHILE

KW - 1,2,4-TRIAZINES

KW - SUBSTITUENTS

KW - SELECTIVITY

KW - PYRIDINES

KW - DIENES

KW - ETHER

M3 - Article

SN - 0040-4020

VL - 51

SP - 11601

EP - 11622

JO - Tetrahedron

JF - Tetrahedron

IS - 42

ER -

INTRAMOLECULAR DIELS-ALDER REACTIONS OF SILYL ACETAL-TETHERED TRIENES

Abstract

Keywords

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