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Rhodium‐Catalyzed Cross‐Aldol Reaction: In Situ Aldehyde‐Enolate Formation from Allyloxyboranes and Primary Allylic Alcohols
Author(s) -
Lin Luqing,
Yamamoto Kumiko,
Matsunaga Shigeki,
Kanai Motomu
Publication year - 2012
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.201205680
Subject(s) - aldol reaction , aldehyde , chemistry , allylic rearrangement , enol , organic chemistry , enantioselective synthesis , isomerization , catalysis , combinatorial chemistry
Dip in! A Rh/dippf catalyst generates aldehyde‐derived enol boranes at ambient temperature by isomerization of allyloxy‐ and homoallyloxyboranes. A one‐pot isomerization/cross ‐ aldol sequence provides aldehyde–aldehyde adducts in good yield with syn selectivity. Direct use of primary allylic and homoallylic alcohols was also achieved.