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Enantio‐ and Diastereoselective Vinylogous Mukaiyama Aldol Reactions of α‐Keto Phosphonates with 2‐(Trimethylsilyloxy)‐ furan Catalyzed by Bis(oxazoline)‐Copper Complexes
Author(s) -
Hou Gang,
Yu Jipan,
Yu Chengbin,
Wu Guiping,
Miao Zhiwei
Publication year - 2013
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.201200810
Subject(s) - chemistry , oxazoline , aldol reaction , furan , phosphonate , dichloromethane , catalysis , copper , organic chemistry , enantioselective synthesis , medicinal chemistry , solvent
The asymmetric vinylogous Mukaiyama aldol reaction between α‐keto phosphonate and 2‐(trimethylsilyloxy)furan was performed by using bis(oxazoline)‐copper complexes as the catalyst and 2,2,2‐trifluoroethanol as additive in dichloromethane. The present method is highly tolerable for functionalized α‐keto phosphonates and enabled us to obtain the corresponding 3‐ and 4‐substituted benzyl‐functionalized tertiary α‐hydroxy phosphonates in high yields (up to 86%) as well as high enantiostereoselectivities (up to 98% ee ) and diastereoselectivities (up to 99:1, anti ‐selective).