Modular synthesis of chiral homo- and heterotrisoxazolines. Improving the enantioselectivity in the asymmetric Michael addition of indole to benzylidene malonate

Meng Chun Ye; Bin Li; Jian Zhou; Xiu Li Sun; Yong Tang

doi:10.1021/jo050595m

Modular synthesis of chiral homo- and heterotrisoxazolines. Improving the enantioselectivity in the asymmetric Michael addition of indole to benzylidene malonate

Meng Chun Ye
, Bin Li
, Jian Zhou
, Xiu Li Sun
, Yong Tang^*

^*Corresponding author for this work

CAS - Shanghai Institute of Organic Chemistry

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

50 Scopus citations

Abstract

A simple approach to a diverse set of chiral trisoxazolines is described. Deprotonation of bisoxazolines 2, followed by treatment of 2- chloromethyloxazolines 3, affords chiral trisoxazolines, including chiral homo- and hetero-trisoxazolines in good to high yields. These trisoxazolines are successfully applied in the asymmetric reaction of indole with benzylidene malonate, and ee's up to 93% were obtained.

Original language	English
Pages (from-to)	6108-6110
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	70
Issue number	15
DOIs	https://doi.org/10.1021/jo050595m
State	Published - 22 Jul 2005
Externally published	Yes

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title = "Modular synthesis of chiral homo- and heterotrisoxazolines. Improving the enantioselectivity in the asymmetric Michael addition of indole to benzylidene malonate",

abstract = "A simple approach to a diverse set of chiral trisoxazolines is described. Deprotonation of bisoxazolines 2, followed by treatment of 2- chloromethyloxazolines 3, affords chiral trisoxazolines, including chiral homo- and hetero-trisoxazolines in good to high yields. These trisoxazolines are successfully applied in the asymmetric reaction of indole with benzylidene malonate, and ee's up to 93\% were obtained.",

author = "Ye, \{Meng Chun\} and Bin Li and Jian Zhou and Sun, \{Xiu Li\} and Yong Tang",

year = "2005",

month = jul,

day = "22",

doi = "10.1021/jo050595m",

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volume = "70",

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journal = "Journal of Organic Chemistry",

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T1 - Modular synthesis of chiral homo- and heterotrisoxazolines. Improving the enantioselectivity in the asymmetric Michael addition of indole to benzylidene malonate

AU - Ye, Meng Chun

AU - Li, Bin

AU - Zhou, Jian

AU - Sun, Xiu Li

AU - Tang, Yong

PY - 2005/7/22

Y1 - 2005/7/22

N2 - A simple approach to a diverse set of chiral trisoxazolines is described. Deprotonation of bisoxazolines 2, followed by treatment of 2- chloromethyloxazolines 3, affords chiral trisoxazolines, including chiral homo- and hetero-trisoxazolines in good to high yields. These trisoxazolines are successfully applied in the asymmetric reaction of indole with benzylidene malonate, and ee's up to 93% were obtained.

AB - A simple approach to a diverse set of chiral trisoxazolines is described. Deprotonation of bisoxazolines 2, followed by treatment of 2- chloromethyloxazolines 3, affords chiral trisoxazolines, including chiral homo- and hetero-trisoxazolines in good to high yields. These trisoxazolines are successfully applied in the asymmetric reaction of indole with benzylidene malonate, and ee's up to 93% were obtained.

UR - https://www.scopus.com/pages/publications/22244469405

U2 - 10.1021/jo050595m

DO - 10.1021/jo050595m

M3 - 文章

AN - SCOPUS:22244469405

SN - 0022-3263

VL - 70

SP - 6108

EP - 6110

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Modular synthesis of chiral homo- and heterotrisoxazolines. Improving the enantioselectivity in the asymmetric Michael addition of indole to benzylidene malonate

Abstract

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