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

Manat Pohmakotr; Nattawut Yotapan; Patoomratana Tuchinda; Chutima Kuhakarn; Vichai Reutrakul

doi:10.1021/jo070533r

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

Manat Pohmakotr
, Nattawut Yotapan
, Patoomratana Tuchinda
, Chutima Kuhakarn
, Vichai Reutrakul

Mahidol University

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

35 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5016-5019
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	13
DOIs	https://doi.org/10.1021/jo070533r
Publication status	Published - 22 Jun 2007
Externally published	Yes

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10.1021/jo070533r

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@article{822d571f9cfe44409017a05c78cee484,

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

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.",

author = "Manat Pohmakotr and Nattawut Yotapan and Patoomratana Tuchinda and Chutima Kuhakarn and Vichai Reutrakul",

year = "2007",

month = jun,

day = "22",

doi = "10.1021/jo070533r",

language = "English",

volume = "72",

pages = "5016--5019",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "13",

}

Highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl esters via Sc(OTf)₃-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines. / Pohmakotr, Manat; Yotapan, Nattawut; Tuchinda, Patoomratana et al.
In: Journal of Organic Chemistry, Vol. 72, No. 13, 22.06.2007, p. 5016-5019.

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

TY - JOUR

T1 - Highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl esters via Sc(OTf)3-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines

AU - Pohmakotr, Manat

AU - Yotapan, Nattawut

AU - Tuchinda, Patoomratana

AU - Kuhakarn, Chutima

AU - Reutrakul, Vichai

PY - 2007/6/22

Y1 - 2007/6/22

N2 - (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.

AB - (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.

UR - https://www.scopus.com/pages/publications/34250885710

U2 - 10.1021/jo070533r

DO - 10.1021/jo070533r

M3 - Article

C2 - 17506584

AN - SCOPUS:34250885710

SN - 0022-3263

VL - 72

SP - 5016

EP - 5019

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

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

Abstract

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