Simple chiral crown ethers complexed with potassium tert-butoxide as efficient catalysts for asymmetric Michael additions

Shin Aoki; Shigeki Sasaki; Kenji Koga

doi:10.1016/S0040-4039(01)93942-5

Simple chiral crown ethers complexed with potassium tert-butoxide as efficient catalysts for asymmetric Michael additions

Shin Aoki, Shigeki Sasaki, Kenji Koga

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

73 Citations (Scopus)

Abstract

Simple C₂-symmetric chiral crown ether 1 complexed with KOtBu was found to work as an efficient chiral catalyst in Michael additions to cause high asymmetric induction. The results with various chiral crown ethers as catalysts suggest that diaxial-like conformation of the vicinal methyl groups of 1·potassium enolate complex is responsible for the chiral induction.

Original language	English
Pages (from-to)	7229-7230
Number of pages	2
Journal	Tetrahedron Letters
Volume	30
Issue number	51
DOIs	https://doi.org/10.1016/S0040-4039(01)93942-5
Publication status	Published - 1989
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)93942-5

Cite this

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title = "Simple chiral crown ethers complexed with potassium tert-butoxide as efficient catalysts for asymmetric Michael additions",

abstract = "Simple C2-symmetric chiral crown ether 1 complexed with KOtBu was found to work as an efficient chiral catalyst in Michael additions to cause high asymmetric induction. The results with various chiral crown ethers as catalysts suggest that diaxial-like conformation of the vicinal methyl groups of 1·potassium enolate complex is responsible for the chiral induction.",

author = "Shin Aoki and Shigeki Sasaki and Kenji Koga",

year = "1989",

doi = "10.1016/S0040-4039(01)93942-5",

language = "English",

volume = "30",

pages = "7229--7230",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "51",

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TY - JOUR

T1 - Simple chiral crown ethers complexed with potassium tert-butoxide as efficient catalysts for asymmetric Michael additions

AU - Aoki, Shin

AU - Sasaki, Shigeki

AU - Koga, Kenji

PY - 1989

Y1 - 1989

N2 - Simple C2-symmetric chiral crown ether 1 complexed with KOtBu was found to work as an efficient chiral catalyst in Michael additions to cause high asymmetric induction. The results with various chiral crown ethers as catalysts suggest that diaxial-like conformation of the vicinal methyl groups of 1·potassium enolate complex is responsible for the chiral induction.

AB - Simple C2-symmetric chiral crown ether 1 complexed with KOtBu was found to work as an efficient chiral catalyst in Michael additions to cause high asymmetric induction. The results with various chiral crown ethers as catalysts suggest that diaxial-like conformation of the vicinal methyl groups of 1·potassium enolate complex is responsible for the chiral induction.

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UR - http://www.scopus.com/inward/citedby.url?scp=0024843407&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)93942-5

DO - 10.1016/S0040-4039(01)93942-5

M3 - Article

AN - SCOPUS:0024843407

SN - 0040-4039

VL - 30

SP - 7229

EP - 7230

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Simple chiral crown ethers complexed with potassium tert-butoxide as efficient catalysts for asymmetric Michael additions

Abstract

All Science Journal Classification (ASJC) codes

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