Intramolecular asymmetric Heck reactions: Evidence for dynamic kinetic resolution effects

Michael C. McDermott; G. Richard Stephenson; David L. Hughes; Andrew J. Walkington

doi:10.1021/ol0606132

Intramolecular asymmetric Heck reactions: Evidence for dynamic kinetic resolution effects

Michael C. McDermott, G. Richard Stephenson, David L. Hughes, Andrew J. Walkington

Chemistry of Materials and Catalysis

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

33 Citations (Scopus)

Abstract

Enantioselectivity of the cyclization of 1 varies at different stages in the reaction. X-ray crystallography has shown that 1 exists as enantiomerically pure (M) and (P) chiral helical structures defined by the relative orientations of the arene, amide, and alkene. The relative rates of interconversion of the rotamers of 1 have been established, leading to mechanistic proposals to account for the variation of ee based on kinetic resolution effects.

Original language	English
Pages (from-to)	2917-2920
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	14
DOIs	https://doi.org/10.1021/ol0606132
Publication status	Published - 2006

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10.1021/ol0606132

Cite this

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title = "Intramolecular asymmetric Heck reactions: Evidence for dynamic kinetic resolution effects",

abstract = "Enantioselectivity of the cyclization of 1 varies at different stages in the reaction. X-ray crystallography has shown that 1 exists as enantiomerically pure (M) and (P) chiral helical structures defined by the relative orientations of the arene, amide, and alkene. The relative rates of interconversion of the rotamers of 1 have been established, leading to mechanistic proposals to account for the variation of ee based on kinetic resolution effects.",

author = "McDermott, {Michael C.} and Stephenson, {G. Richard} and Hughes, {David L.} and Walkington, {Andrew J.}",

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AU - Stephenson, G. Richard

AU - Hughes, David L.

AU - Walkington, Andrew J.

PY - 2006

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AB - Enantioselectivity of the cyclization of 1 varies at different stages in the reaction. X-ray crystallography has shown that 1 exists as enantiomerically pure (M) and (P) chiral helical structures defined by the relative orientations of the arene, amide, and alkene. The relative rates of interconversion of the rotamers of 1 have been established, leading to mechanistic proposals to account for the variation of ee based on kinetic resolution effects.

U2 - 10.1021/ol0606132

DO - 10.1021/ol0606132

M3 - Article

VL - 8

SP - 2917

EP - 2920

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 14

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