Asymmetric Wittig reaction of chiral arsonium ylides - I. Asymmetric olefination of 4-substituted cyclohexanones

Wei Min Dai; Jinlong Wu; Xian Huang

doi:10.1016/S0957-4166(97)00223-1

Asymmetric Wittig reaction of chiral arsonium ylides - I. Asymmetric olefination of 4-substituted cyclohexanones

Wei Min Dai
, Jinlong Wu
, Xian Huang

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

43 Citations (Scopus)

Abstract

Asymmetric Wittig-type olefination of 4-substituted cyclohexanones with chiral ligand-modified stable arsonium ylides has been examined. The 8-phenylmenthol-derived chiral arsonium ylide of 4 reacted with prochiral ketones 9a-d at -15°C to give the 4-substituted cyclohexylideneacetates 11a-d in 58-69% yield and in up to 80% diastereomeric excess (de).

Original language	English
Pages (from-to)	1979-1982
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	8
Issue number	12
DOIs	https://doi.org/10.1016/S0957-4166(97)00223-1
Publication status	Published - 27 Jun 1997
Externally published	Yes

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10.1016/S0957-4166(97)00223-1

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title = "Asymmetric Wittig reaction of chiral arsonium ylides - I. Asymmetric olefination of 4-substituted cyclohexanones",

abstract = "Asymmetric Wittig-type olefination of 4-substituted cyclohexanones with chiral ligand-modified stable arsonium ylides has been examined. The 8-phenylmenthol-derived chiral arsonium ylide of 4 reacted with prochiral ketones 9a-d at -15°C to give the 4-substituted cyclohexylideneacetates 11a-d in 58-69\% yield and in up to 80\% diastereomeric excess (de).",

author = "Dai, \{Wei Min\} and Jinlong Wu and Xian Huang",

year = "1997",

month = jun,

day = "27",

doi = "10.1016/S0957-4166(97)00223-1",

language = "English",

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pages = "1979--1982",

journal = "Tetrahedron Asymmetry",

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T1 - Asymmetric Wittig reaction of chiral arsonium ylides - I. Asymmetric olefination of 4-substituted cyclohexanones

AU - Dai, Wei Min

AU - Wu, Jinlong

AU - Huang, Xian

PY - 1997/6/27

Y1 - 1997/6/27

N2 - Asymmetric Wittig-type olefination of 4-substituted cyclohexanones with chiral ligand-modified stable arsonium ylides has been examined. The 8-phenylmenthol-derived chiral arsonium ylide of 4 reacted with prochiral ketones 9a-d at -15°C to give the 4-substituted cyclohexylideneacetates 11a-d in 58-69% yield and in up to 80% diastereomeric excess (de).

AB - Asymmetric Wittig-type olefination of 4-substituted cyclohexanones with chiral ligand-modified stable arsonium ylides has been examined. The 8-phenylmenthol-derived chiral arsonium ylide of 4 reacted with prochiral ketones 9a-d at -15°C to give the 4-substituted cyclohexylideneacetates 11a-d in 58-69% yield and in up to 80% diastereomeric excess (de).

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:A1997XJ79100010

UR - https://openalex.org/W2065877124

U2 - 10.1016/S0957-4166(97)00223-1

DO - 10.1016/S0957-4166(97)00223-1

M3 - Journal Article

SN - 0957-4166

VL - 8

SP - 1979

EP - 1982

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 12

ER -

Asymmetric Wittig reaction of chiral arsonium ylides - I. Asymmetric olefination of 4-substituted cyclohexanones

Abstract

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