Enantioselective addition of diethylzinc to aldehydes catalyzed by Titanium(IV) complexes of N-sulfonylated β-amino alcohols with four stereogenic centers

被引：25

作者：

Hsieh, Shengh-Siang ^{[1
]}

Gau, Han-Mou ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

来源：

CHIRALITY | 2006年 / 18卷 / 08期

关键词：

titanium(IV) complex; N-sulfonylated beta-amino alcohol; diethylzinc; aldehyde; asymmetric alkylation reaction;

D O I：

10.1002/chir.20279

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An N-sulfonylated beta-amino alcohol (R,S,S,R)-9 with four stereogenic centers is prepared. The titanium complex of 9 is an effective catalyst to induce excellent enantioselectivities for diethylzinc addition to aromatic aldehydes with ee values up to 99%. The feature of doubling the quantity of Ti(O-i-Pr)(4) required relative to the catalytic system of the Ti complex of bidentate N-sulfonylated beta-amino alcohols suggests that the two N-sulfonylated beta-amino alcohol moieties in 9 behave as two independent bidentate ligands in the catalytic system. The results obtained using ligand 15 having one N-sulfonylated beta-amino alcohol blocked support the argument of two independent active bidentate moieties in 9.

引用

页码：569 / 574

页数：6

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