Ruthenium‐Catalyzed Tandem Olefin Migration/Aldol and Mannich‐Type Reactions in Water and Protic Solvents | Zendy

Wang Mingwen | Zendy; Yang XiaoFan | Zendy; Li ChaoJun | Zendy

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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)

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