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Oxy Effects on the Platinum‐Catalyzed Carbo‐ and Oxacyclizations of 2‐Oxiranyl‐1‐(1‐oxyalk‐2‐ynyl)benzenes
Author(s) -
Chaudhuri Rupsha,
Pawar Samir Kundlik,
Pati Kamalkishore,
Liu RaiShung
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200187
Subject(s) - chemistry , intramolecular force , catalysis , platinum , bicyclic molecule , alkyl , medicinal chemistry , stereochemistry , organic chemistry
We report new platinum‐catalyzed protocols for the synthesis of carbocycles and oxacycles from 2‐oxiranyl‐1‐(1‐oxyalk‐2‐ynyl)benzenes. For 1,2,2‐trisubstituted epoxides bearing an acyloxy group, their platinum‐catalyzed cyclizations proceed through an initial 1,3‐acyloxy shift, followed by an intramolecular attack of an allenyl acetate at the carbonyl group, ultimately giving 2‐naphthyl ketones through a selective 1,2‐alkyl shift. 1,1‐Disubstituted epoxides bearing a siloxy group undergo an oxacyclization to give bicyclic ketals with high diastereoselectivity.