Modular pyridine-type P,N-ligands derived from monoterpenes:: application in asymmetric Heck addition

被引:61
作者
Malkov, AV [1 ]
Bella, M [1 ]
Stará, IG [1 ]
Kocovsky, P [1 ]
机构
[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland
关键词
D O I
10.1016/S0040-4039(01)00369-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel (diphenylphosphinophenyl)pyridine ligands (+)-8, (+)-15, (-)-21, and (-)-26 were synthesized from (-)-beta -pinene, (+)-3-carene, (+)-2-carene, and (-)-alpha -pinene, respectively, via Krohnke annulation as the key step, and shown to effect less than or equal to 88% ee in Heck addition (27 --> 28). Ligands (+)-15 and (-)-21 are quasi-enantiomeric; ligands 8 and 26 can be prepared in both enantiomeric forms from (+)- and (-)-enantiomers of alpha- and beta -pinene, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.
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页码:3045 / 3048
页数:4
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