5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a new class of recoverable chiral auxiliary

Yoshinori Yamamoto; Hirofumi Kin; Ichiro Suzuki; Naoki Asao

doi:10.1016/0040-4039(96)00137-2

5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a new class of recoverable chiral auxiliary

Yoshinori Yamamoto, Hirofumi Kin, Ichiro Suzuki, Naoki Asao

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

7 Citations (Scopus)

Abstract

Reduction of α-ketoesters bearing 5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a chiral auxillary proceeds with high diastereoselectivity by using DIBAL as a reducing agent. The chiral auxiliary is recovered upon treatment with base, and α-hydroxy carboxylic acids are obtained in good al yields with high enantioselectivity.

Original language	English
Pages (from-to)	1863-1866
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	11
DOIs	https://doi.org/10.1016/0040-4039(96)00137-2
Publication status	Published - 1996 Mar 11
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a new class of recoverable chiral auxiliary",

abstract = "Reduction of α-ketoesters bearing 5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a chiral auxillary proceeds with high diastereoselectivity by using DIBAL as a reducing agent. The chiral auxiliary is recovered upon treatment with base, and α-hydroxy carboxylic acids are obtained in good al yields with high enantioselectivity.",

author = "Yoshinori Yamamoto and Hirofumi Kin and Ichiro Suzuki and Naoki Asao",

year = "1996",

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T1 - 5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a new class of recoverable chiral auxiliary

AU - Yamamoto, Yoshinori

AU - Kin, Hirofumi

AU - Suzuki, Ichiro

AU - Asao, Naoki

PY - 1996/3/11

Y1 - 1996/3/11

N2 - Reduction of α-ketoesters bearing 5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a chiral auxillary proceeds with high diastereoselectivity by using DIBAL as a reducing agent. The chiral auxiliary is recovered upon treatment with base, and α-hydroxy carboxylic acids are obtained in good al yields with high enantioselectivity.

AB - Reduction of α-ketoesters bearing 5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a chiral auxillary proceeds with high diastereoselectivity by using DIBAL as a reducing agent. The chiral auxiliary is recovered upon treatment with base, and α-hydroxy carboxylic acids are obtained in good al yields with high enantioselectivity.

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U2 - 10.1016/0040-4039(96)00137-2

DO - 10.1016/0040-4039(96)00137-2

M3 - Article

AN - SCOPUS:0029993774

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EP - 1866

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 11

ER -

5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a new class of recoverable chiral auxiliary

Abstract

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