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Catalytic Asymmetric Allylic Transfer Reactions for the Enantioselective Synthesis of Dienyl and Enynyl Alcohols
Author(s) -
Yu ChanMo,
Jeon Miyoo,
Lee JaeYoung,
Jeon Junha
Publication year - 2001
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 - 10.1002/1099-0690(200103)2001:6<1143::aid-ejoc1143>3.0.co;2-o
Subject(s) - enantioselective synthesis , chemistry , allylic rearrangement , catalysis , reagent , organic chemistry , combinatorial chemistry
Efficient catalytic asymmetric allylic transfer reactions of achiral aldehydes with 2‐ethynyl‐ and 2‐ethenyl‐2‐propenylstannane promoted by BINOL‐Ti IV complex with synergetic reagent are achieved for the synthesis of homoenynyl‐ and dienyl alcohols with high levels of enantioselectivity. The range of enantioselectivity is 84−99% ee with good chemical yields. The application of catalytic asymmetric dienylation in a single operation was exemplified by the enantioselective synthesis of naturally occurring (−)‐Ipsdienol and (−)‐Ipsenol.