Enantioselective addition of organozinc reagents to aldehydes catalyzed by 3,3′-bis(diphenylphosphinoyl)-BINOL
Enantioselective addition of organozinc reagents to aldehydes catalyzed by 3,3′-bis(diphenylphosphinoyl)-BINOL
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DOI：
10.1002/adsc.200505221
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发表时间：
2005-10-01
影响因子：
5.4
通讯作者：
Ishihara, K
中科院分区：
文献类型：
--
作者：
Hatano, M;Miyamoto, T;Ishihara, K
有机锌试剂与芳香族和脂肪族醛I的对映选择性加成反应通过使用（R）-3，3 '-双（二苯基膦酰基）-BINOL（3）或（R）-3，3'-双（二苯基硫代膦酰基）-BINOL（4）而无Ti（IV）配合物的催化以高产率得到具有优异对映选择性的仲醇2。含BINOL骨架的（硫代）膦酰基的O或S原子与有机锌试剂配位可有效地提高有机锌试剂的亲核性。
The enantioselective addition of organozinc reagents to aromatic and aliphatic aldehydes I gives secondary alcohols 2 with excellent enantioselectivities in high yields through the catalytic use of (R)-3,3'-bis(diphenylphosphinoyl)-BINOL (3) or (R)-3,3'-bis(diphenylthiophosphinoyl)-BINOL (4) without Ti(IV) complexes. The coordination of the O or S atom of a (thio)phosphinoyl group bearing a BINOL backbone to organozinc reagents can efficiently increase the nucleophilicity of the organozinc reagents.