Asymmetric synthesis of cis-5-substituted pyrrolidine 2-phosphonates using metal carbenoid NH insertion and delta-amino beta-ketophosphonates

Franklin A Davis; Yongzhong Wu; He Xu; Junyi Zhang

doi:10.1021/ol048157+

Asymmetric synthesis of cis-5-substituted pyrrolidine 2-phosphonates using metal carbenoid NH insertion and delta-amino beta-ketophosphonates

Org Lett. 2004 Nov 25;6(24):4523-5. doi: 10.1021/ol048157+.

Authors

Franklin A Davis¹, Yongzhong Wu, He Xu, Junyi Zhang

Affiliation

¹ Department of Chemistry, Temple University, Philadelphia, PA 19122, USA. [email protected]

PMID: 15548066
DOI: 10.1021/ol048157+

Abstract

Cis-5-substituted pyrrolidine phosphonates, proline surrogates, are prepared by a highly stereoselective intramolecular metal carbenoid N-H insertion from a sulfinimine-derived delta-amino alpha-diazo beta-ketophosphonate. [reaction: see text]

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Amines / chemistry
Metals
Organophosphonates / chemical synthesis*
Pyrrolidines / chemical synthesis*

Substances

Amines
Metals
Organophosphonates
Pyrrolidines

Grants and funding

GM 57870/GM/NIGMS NIH HHS/United States