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Ruthenium‐Catalyzed Tandem Olefin Migration/Aldol and Mannich‐Type Reactions in Water and Protic Solvents
Author(s) -
Wang Mingwen,
Yang XiaoFan,
Li ChaoJun
Publication year - 2003
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/ejoc.200390155
Subject(s) - aldol reaction , chemistry , aldehyde , catalysis , diastereomer , tandem , olefin fiber , organic chemistry , toluene , alcohol , ruthenium , medicinal chemistry , materials science , composite material
Cross‐coupling between 3‐buten‐2‐ol ( 2 ) and aldehyde in the presence of a catalytic amount of [RuCl 2 (PPh 3 ) 3 ] has been developed, through a tandem olefin migration/aldol reaction in a water/toluene mixture. The presence of In(OAc) 3 promoted the aldol reaction with α‐vinylbenzyl alcohol ( 4 ) and aldehyde, while treatment of 3‐buten‐2‐ol ( 2 ) with imines generated Mannich‐type reaction products; syn isomers were formed as the major diastereomers for the aldol products 3a − 3g and 5a − 5e and the Mannich products 7a − 7g . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)