Premium
Gold(I)‐Catalyzed Asymmetric Cycloisomerization of Eneallenes into Vinylcyclohexenes
Author(s) -
Tarselli Michael A.,
Chianese Anthony R.,
Lee Stephen J.,
Gagné Michel R.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701959
Subject(s) - cycloisomerization , cationic polymerization , catalysis , chemistry , amide , alcohol , medicinal chemistry , organic chemistry , stereochemistry , combinatorial chemistry
Coming around : Cycloisomerization of eneallenes by cationic gold(I) catalysts produces vinylcyclohexene derivatives in up to 77 % ee , using [3,5‐xylyl‐binap(AuCl) 2 ] and AgOTf additive (see scheme; 3,5‐xylyl‐binap=2,2′‐bis(di(3,5‐xylyl)phosphino)‐1,1′‐binaphthyl). The procedure is amenable to the synthesis of mono‐ and bicyclic products and is tolerant of ester, alcohol, and amide groups.