Photochemical Reaction between Tertiary Allylic Amines and Chromium Carbene Complexes:  Synthesis of Lactams via a Zwitterion Aza Cope Rearrangement

1996 ◽  
Vol 61 (8) ◽  
pp. 2871-2876 ◽  
Author(s):  
Christopher J. Deur ◽  
Michael W. Miller ◽  
Louis S. Hegedus

The photochemical reaction of chromium carbene complexes with imines has been developed into an efficient process for the synthesis of β-lactams. A new route to aminocarbene complexes, involving the reaction of Na 2 Cr(CO) 5 with amides and trimethylsilyl chloride has been developed. By using this procedure, chiral, optically active aminocarbene complexes have been prepared, and their photochemical reactions with imines developed. Chiral, optically active β-lactams have been prepared with more than 90% diastereoselectivity by this procedure. Chiral, optically active aminocarbene complexes containing pendent alcohol groups have also been prepared. Photolysis of these produces aminolactones, which can be cleaved to natural and unnatural α-amino acids.


1997 ◽  
Vol 38 (39) ◽  
pp. 6787-6790 ◽  
Author(s):  
Craig A. Merlic ◽  
Daniel M. McInnes ◽  
Ying You

2003 ◽  
Vol 294 (2) ◽  
pp. 129-139 ◽  
Author(s):  
Jordi Poater ◽  
Montserrat Cases ◽  
Xavier Fradera ◽  
Miquel Duran ◽  
Miquel Solà

Sign in / Sign up

Export Citation Format

Share Document