Asymmetric synthesis of beta-amino carbonyl compounds with N-sulfinyl beta-amino Weinreb amides.
[reaction: see text] Diverse organometallic reagents readily add to enantiopure N-sulfinyl beta-amino Weinreb amides providing the corresponding, stable, N-sulfinyl beta-amino carbonyl compounds in good to excellent yields. This new methodology represents a general solution to the problem of beta-amino carbonyl syntheses, which are important chiral building blocks and constituents of natural products. N-Sulfinyl beta-amino Weinreb amides are prepared by reaction of the potassium enolate of N-methoxy N-methylacetamide with sulfinimines (N-sulfinyl imines) or lithium N,O-dimethylhydroxylamine with N-sulfinyl beta-amino esters.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Nolt
M Brad
MB
Wu
Yongzhong
Y
Prasad
Kavirayani R
KR
Li
Danyang
D
Yang
Bin
B
Bowen
Kerisha
K
Lee
Seung H
SH
Eardley
John H
JH
D000447:Aldehydes / Q000138:chemical synthesis*; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
D000447:Aldehydes; D000577:Amides; D007659:Ketones; D013454:Sulfoxides