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The Formation of Silylated β‐Lactams from Silylketenes through Lewis Acid Promoted [2+2] Cycloaddition: A Combined Theoretical and Experimental Study
Author(s) -
Pelotier Béatrice,
Rajzmann Michel,
Pons JeanMarc,
Campomanes Pablo,
López Ramón,
Sordo Tomás L.
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400907
Subject(s) - ketene , chemistry , trimethylsilyl , lewis acids and bases , cycloaddition , catalysis , stereoselectivity , medicinal chemistry , stereochemistry , organic chemistry
The stereoselective formation of silylated cis ‐β‐lactams from (trimethylsilyl)ketene and an α‐imino ester by Lewis acid catalysis is described. Theoretical results suggest that the reaction between (trimethylsilyl)ketene and trans ‐(methoxycarbonyl)‐ N ‐methylformaldimine would proceed most favourably with the BF 3 catalyst coordinated to the ketene. Moreover, the calculated energy barriers account for the cis : trans ratio found experimentally. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)