An improved method for the stereoselective synthesis of β-lactams from carboxylic acids and imines

Gunda I. Georg; Peter M. Mashava; Xiangming Guan

doi:10.1016/S0040-4039(00)74832-5

An improved method for the stereoselective synthesis of β-lactams from carboxylic acids and imines

Gunda I. Georg, Peter M. Mashava, Xiangming Guan

Medicinal Chemistry

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

56 Scopus citations

Abstract

Carboxylic acids activated with Mukaiyama's reagent (2-chloro-N-methylpyridinium iodide) reacted with imines to produce β-lactams in good yields and with high stereoselectivity. The utilization of three equivalents of tripropylamine as the base was necessary to obtain high chemical yield and good stereoselectivity.

Original language	English (US)
Pages (from-to)	581-584
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4039(00)74832-5
State	Published - Jan 28 1991

Bibliographical note

Funding Information:
Financial assrstance is acknowledged from the National Institute of Health (GM 42260) and the Btomedtcal Research Grant (RR 5606) at the University of Kansas We arc also grateful to the Afrtcan-American Institute, New York for a Post-Graduate Award to P M Mashavd WC wtsh to thank Mark Mrlstead for the synthesis of h-lactam 3h.

Access

10.1016/S0040-4039(00)74832-5

OpenUrl availability

Full text

Cite this

@article{27328ac3b89a4c52a94cad84983a7d10,

title = "An improved method for the stereoselective synthesis of β-lactams from carboxylic acids and imines",

abstract = "Carboxylic acids activated with Mukaiyama's reagent (2-chloro-N-methylpyridinium iodide) reacted with imines to produce β-lactams in good yields and with high stereoselectivity. The utilization of three equivalents of tripropylamine as the base was necessary to obtain high chemical yield and good stereoselectivity.",

author = "Georg, {Gunda I.} and Mashava, {Peter M.} and Xiangming Guan",

note = "Funding Information: Financial assrstance is acknowledged from the National Institute of Health (GM 42260) and the Btomedtcal Research Grant (RR 5606) at the University of Kansas We arc also grateful to the Afrtcan-American Institute, New York for a Post-Graduate Award to P M Mashavd WC wtsh to thank Mark Mrlstead for the synthesis of h-lactam 3h.",

year = "1991",

month = jan,

day = "28",

doi = "10.1016/S0040-4039(00)74832-5",

language = "English (US)",

volume = "32",

pages = "581--584",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "5",

}

TY - JOUR

T1 - An improved method for the stereoselective synthesis of β-lactams from carboxylic acids and imines

AU - Georg, Gunda I.

AU - Mashava, Peter M.

AU - Guan, Xiangming

N1 - Funding Information: Financial assrstance is acknowledged from the National Institute of Health (GM 42260) and the Btomedtcal Research Grant (RR 5606) at the University of Kansas We arc also grateful to the Afrtcan-American Institute, New York for a Post-Graduate Award to P M Mashavd WC wtsh to thank Mark Mrlstead for the synthesis of h-lactam 3h.

PY - 1991/1/28

Y1 - 1991/1/28

N2 - Carboxylic acids activated with Mukaiyama's reagent (2-chloro-N-methylpyridinium iodide) reacted with imines to produce β-lactams in good yields and with high stereoselectivity. The utilization of three equivalents of tripropylamine as the base was necessary to obtain high chemical yield and good stereoselectivity.

AB - Carboxylic acids activated with Mukaiyama's reagent (2-chloro-N-methylpyridinium iodide) reacted with imines to produce β-lactams in good yields and with high stereoselectivity. The utilization of three equivalents of tripropylamine as the base was necessary to obtain high chemical yield and good stereoselectivity.

UR - http://www.scopus.com/inward/record.url?scp=0026088008&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0026088008&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)74832-5

DO - 10.1016/S0040-4039(00)74832-5

M3 - Article

AN - SCOPUS:0026088008

SN - 0040-4039

VL - 32

SP - 581

EP - 584

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

An improved method for the stereoselective synthesis of β-lactams from carboxylic acids and imines

Abstract

Bibliographical note

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this