Asymmetric synthesis of the β-lactam framework via a three-component coupling reaction

Naoki Asao; Naofumi Tsukada; Yoshinori Yamamoto

doi:10.1039/C39930001660

Asymmetric synthesis of the β-lactam framework via a three-component coupling reaction

Naoki Asao, Naofumi Tsukada, Yoshinori Yamamoto

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

21 Citations (Scopus)

Abstract

The reaction of the chiral lithium amide 4 with the dienoate 5a provides regio- and stereo-selectively the β-amino ester 8 in essentially quantitative yield with >99% diastereoisomeric excess, which can be converted upon sequential treatment with LiNPrⁱ₂-B(OMe) ₃-MeCHO to the key intermediate 6 for the β-lactam 7 having the correct absolute configuration.

Original language	English
Pages (from-to)	1660-1662
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	21
DOIs	https://doi.org/10.1039/C39930001660
Publication status	Published - 1993 Dec 1

ASJC Scopus subject areas

Molecular Medicine

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10.1039/C39930001660

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title = "Asymmetric synthesis of the β-lactam framework via a three-component coupling reaction",

abstract = "The reaction of the chiral lithium amide 4 with the dienoate 5a provides regio- and stereo-selectively the β-amino ester 8 in essentially quantitative yield with >99% diastereoisomeric excess, which can be converted upon sequential treatment with LiNPri2-B(OMe) 3-MeCHO to the key intermediate 6 for the β-lactam 7 having the correct absolute configuration.",

author = "Naoki Asao and Naofumi Tsukada and Yoshinori Yamamoto",

year = "1993",

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doi = "10.1039/C39930001660",

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N2 - The reaction of the chiral lithium amide 4 with the dienoate 5a provides regio- and stereo-selectively the β-amino ester 8 in essentially quantitative yield with >99% diastereoisomeric excess, which can be converted upon sequential treatment with LiNPri2-B(OMe) 3-MeCHO to the key intermediate 6 for the β-lactam 7 having the correct absolute configuration.

AB - The reaction of the chiral lithium amide 4 with the dienoate 5a provides regio- and stereo-selectively the β-amino ester 8 in essentially quantitative yield with >99% diastereoisomeric excess, which can be converted upon sequential treatment with LiNPri2-B(OMe) 3-MeCHO to the key intermediate 6 for the β-lactam 7 having the correct absolute configuration.

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Asymmetric synthesis of the β-lactam framework via a three-component coupling reaction

Abstract

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