Publication:
Highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl esters via Sc(OTf)<inf>3</inf>-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines

Issued Date

2007-06-22

Resource Type

Article

ISSN

00223263

DOI

10.1021/jo070533r

Other identifier(s)

2-s2.0-34250885710

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Journal of Organic Chemistry. Vol.72, No.13 (2007), 5016-5019

Suggested Citation

Manat Pohmakotr, Nattawut Yotapan, Patoomratana Tuchinda, Chutima Kuhakarn, Vichai Reutrakul Highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl esters via Sc(OTf)<inf>3</inf>-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines. Journal of Organic Chemistry. Vol.72, No.13 (2007), 5016-5019. doi:10.1021/jo070533r Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/24348

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Title

Highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl esters via Sc(OTf)<inf>3</inf>-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines

Author(s)

Manat Pohmakotr
 Nattawut Yotapan
 Patoomratana Tuchinda
 Chutima Kuhakarn
 Vichai Reutrakul

Other Contributor(s)

Mahidol University

Abstract

(Chemical Equation Presented) Functionalized γ-lactams are found to be crucial intermediates in the synthesis of biologically important natural products. We herein described a highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl ester derivatives, in high yields with high diastereomeric ratio, via the Mukaiyama-aldol type reaction of 2,5-bis(trimethysilyloxy)furan with imines, employing Sc(OTf)3 as a catalyst. © 2007 American Chemical Society.

Keyword(s)

Chemistry

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/24348

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Scopus 2006-2010