Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines.
Beilstein J Org Chem
; 9: 2675-80, 2013.
Article
in En
| MEDLINE
| ID: mdl-24367432
ABSTRACT
ß-Lactams were diastereoselectively formed by the reaction of SF5-containing aldimines, or an SF5-containing ketimine, with benzyloxyketene in a conrotatory ring closure process. Imine formation and cyclization were possible in spite of the acidification of protons on the carbon bound to SF5. The reactions of the aldimines demonstrated very good 1,2-lk diastereoselectivity, however lack of stereochemical control of the C-N ketimine geometry was reflected in the stereochemistry of the product ß-lactam. Cyclization of imines with a stereogenic center bearing SF5 was reflected in the 1,2-lk,lk selectivity of the ß-lactam.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Beilstein J Org Chem
Year:
2013
Document type:
Article
Affiliation country: