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Platinum‐Catalyzed Cyclization of N ‐Allyl Carbamates for the Synthesis of 5‐Vinyloxazolidinones
Author(s) -
Yoon HyoSang,
Kim JuHye,
Kang Eun Joo,
Jang HyeYoung
Publication year - 2012
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.201101799
Subject(s) - chemistry , nucleophile , platinum , carbamate , catalysis , electrophile , bromide , allyl bromide , vinyl bromide , oxygen , medicinal chemistry , organic chemistry
Platinum‐catalyzed addition of the oxygen nucleophile of a carbamate to an allyl bromide was carried out to afford a range of biologically active 5‐vinyl‐substituted oxazolidinones in good yields. Over the course of the reaction, a platinum complex, SnCl 2 , and the allyl bromide are assumed to generate an electrophilic allyl‐platinum intermediate in the presence of carbamate oxygen nucleophiles. This method provides a wide range of 5‐vinyloxazolidinones regardless of the substitution at the nitrogen and oxygen atoms.