Stereoselective synthesis of 1,2,3,4-tetrasubstituted dienes from allenoates and aldehydes: An observation of phosphine-induced chemoselectivity

Silong Xu; Wen Zou; Guiping Wu; Haibin Song; Zhengjie He

doi:10.1021/ol101429z

Stereoselective synthesis of 1,2,3,4-tetrasubstituted dienes from allenoates and aldehydes: An observation of phosphine-induced chemoselectivity

Silong Xu
, Wen Zou
, Guiping Wu
, Haibin Song
, Zhengjie He

Nankai University

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

47 Scopus citations

Abstract

(Equation Presented). Phosphine-mediated olefination between α-substituted allenoates and aldehydes to form 1,2,3,4-tetrasubstituted 1,3-dienes is presented. High levels of chemo-and diastereoselectivity and yield are obtained for a wide scope of substrates with the choice of appropriate phosphines. This reaction evidences the capacity of phosphines in the control of reaction pathways and provides a highly efficient synthetic method for tetrasubstituted conjugated dienes.

Original language	English
Pages (from-to)	3556-3559
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	15
DOIs	https://doi.org/10.1021/ol101429z
State	Published - 6 Aug 2010
Externally published	Yes

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10.1021/ol101429z

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title = "Stereoselective synthesis of 1,2,3,4-tetrasubstituted dienes from allenoates and aldehydes: An observation of phosphine-induced chemoselectivity",

abstract = "(Equation Presented). Phosphine-mediated olefination between α-substituted allenoates and aldehydes to form 1,2,3,4-tetrasubstituted 1,3-dienes is presented. High levels of chemo-and diastereoselectivity and yield are obtained for a wide scope of substrates with the choice of appropriate phosphines. This reaction evidences the capacity of phosphines in the control of reaction pathways and provides a highly efficient synthetic method for tetrasubstituted conjugated dienes.",

author = "Silong Xu and Wen Zou and Guiping Wu and Haibin Song and Zhengjie He",

year = "2010",

month = aug,

day = "6",

doi = "10.1021/ol101429z",

language = "英语",

volume = "12",

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journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Stereoselective synthesis of 1,2,3,4-tetrasubstituted dienes from allenoates and aldehydes

T2 - An observation of phosphine-induced chemoselectivity

AU - Xu, Silong

AU - Zou, Wen

AU - Wu, Guiping

AU - Song, Haibin

AU - He, Zhengjie

PY - 2010/8/6

Y1 - 2010/8/6

N2 - (Equation Presented). Phosphine-mediated olefination between α-substituted allenoates and aldehydes to form 1,2,3,4-tetrasubstituted 1,3-dienes is presented. High levels of chemo-and diastereoselectivity and yield are obtained for a wide scope of substrates with the choice of appropriate phosphines. This reaction evidences the capacity of phosphines in the control of reaction pathways and provides a highly efficient synthetic method for tetrasubstituted conjugated dienes.

AB - (Equation Presented). Phosphine-mediated olefination between α-substituted allenoates and aldehydes to form 1,2,3,4-tetrasubstituted 1,3-dienes is presented. High levels of chemo-and diastereoselectivity and yield are obtained for a wide scope of substrates with the choice of appropriate phosphines. This reaction evidences the capacity of phosphines in the control of reaction pathways and provides a highly efficient synthetic method for tetrasubstituted conjugated dienes.

UR - https://www.scopus.com/pages/publications/77955156821

U2 - 10.1021/ol101429z

DO - 10.1021/ol101429z

M3 - 文章

C2 - 20670020

AN - SCOPUS:77955156821

SN - 1523-7060

VL - 12

SP - 3556

EP - 3559

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Stereoselective synthesis of 1,2,3,4-tetrasubstituted dienes from allenoates and aldehydes: An observation of phosphine-induced chemoselectivity

Abstract

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