Camphor-based Schiff base ligand SBAIB: an enantioselective catalyst for addition of phenylacetylene to aldehydes

被引：29

作者：

Boobalan, Ramalingam ^{[1
]}

Chen, Chinpiao ^{[1
]}

Lee, Gene-Hsian ^{[2
]}

机构：

[1] Natl Dong Hwa Univ, Dept Chem, Soufeng 974, Hualien, Taiwan

[2] Natl Taiwan Univ, Coll Sci, Instrumentat Ctr, Taipei 106, Taiwan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 08期

关键词：

ASYMMETRIC ALKYNYLATION; PROPARGYLIC ALCOHOLS; ORGANOZINC REAGENTS; ALKYNE ADDITIONS; TERMINAL ALKYNES; ALKYNYLZINC; ACETYLIDES; KETONES; LITHIUM; FACILE;

D O I：

10.1039/c1ob06683h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of Schiff base ligands were synthesized from (1R)-camphor. Under the optimal conditions, (+)-SBAIB-a, 10 was found to be an excellent catalyst for the enantioselective addition of phenylacetylene to various aldehydes without utilizing either achiral additives or Ti((OPr)-Pr-i)(4). This approach yielded (R)-propargylic alcohols in extremely high yields (up to 99%) and excellent enantioselectivities (up to 92%). The corresponding (S)-propargylic alcohols were synthesized in good to high enantioselectivities (up to 91%) and excellent yields (up to 99%) using (-)-SBAIB-a, 41.

引用

页码：1625 / 1638

页数：14

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