Novel chiral 1-(ferrocenylalkyl)-(S)-prolinols and their application in enantioselective synthesis

被引：16
作者：
Gotov, B
Toma, S [1 ]
Solcániová, E
Cvengros, J
机构：
[1] Comenius Univ, Fac Nat Sci, Dept Organ Chem, Bratislava 84215, Slovakia
[2] Comenius Univ, Fac Nat Sci, Inst Chem, Bratislava 84215, Slovakia
来源：
TETRAHEDRON | 2000年 / 56卷 / 04期
关键词：
enantioselective synthesis; ferrocenylphosphine ligands; prolinol;
D O I：
10.1016/S0040-4020(99)01040-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diastereomeric ferrocenylphosphine ligands, (-)-(S,R,pS)-BPPF-Pro (3a) and (+)-(S,S,pR)-BPPF-Pro (3b), containing the (S)-prolinol moiety were prepared. A detailed structural elucidation of these ligands was carried out using NMR. The Pd-complexes of these ligands were used for enantioselective catalysis of allylic substitution reactions of rac-(E)-1,3-diphenyl-3-acetoxyprop-1-ene with C-nucleophiles generated from pentan-2,4-dione and dimethyl malonate. A series of chiral ferrocene aminoalcohols with (S)-prolinol moiety (4a-c) were also prepared. The role of the configuration of stereogenic centers for stereoselectivity in diethylzinc addition to benzaldehyde was studied. (C) 2000 Elsevier Science Ltd. All rights reserved.
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页码：671 / 675
页数：5
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