Asymmetric induction via short-lived chiral enolates with a chiral C-O axis

Tomoyuki Yoshimura; Keisuke Tomohara; Takeo Kawabata

doi:10.1021/ja4018122

Asymmetric induction via short-lived chiral enolates with a chiral C-O axis

Tomoyuki Yoshimura, Keisuke Tomohara, Takeo Kawabata

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

22 Citations (Scopus)

Abstract

A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be ∼1 s at -78 C.

Original language	English
Pages (from-to)	7102-7105
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	19
DOIs	https://doi.org/10.1021/ja4018122
Publication status	Published - May 15 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja4018122

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title = "Asymmetric induction via short-lived chiral enolates with a chiral C-O axis",

abstract = "A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be ∼1 s at -78 C.",

author = "Tomoyuki Yoshimura and Keisuke Tomohara and Takeo Kawabata",

year = "2013",

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AU - Kawabata, Takeo

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AB - A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be ∼1 s at -78 C.

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Asymmetric induction via short-lived chiral enolates with a chiral C-O axis

Abstract

All Science Journal Classification (ASJC) codes

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