Design of Threonine-Derived Amino Sulfonamide Organocatalysts for the Highly Stereoselective Aldol Reactions

被引：2
|
作者：
Hikawa, Ryoga [1 ]
Shimogaki, Mio [2 ]
Kano, Taichi [1 ]
机构：
[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Tokyo 1848588, Japan
[2] Univ Hyogo, Grad Sch Sci, Kobe, Hyogo 6781297, Japan
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 12卷 / 08期
关键词：
amino acid derivatives; amino sulfonamide; asymmetric aldol reaction; organocatalysis; threonine; CATALYTIC ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE ORGANOCATALYSTS; PROLINE DERIVATIVES; ANTI-MANNICH; KETONES; ACIDS; N-(P-DODECYLPHENYLSULFONYL)-2-PYRROLIDINECARBOXAMIDE; EFFICIENT; SCOPE;
D O I：
10.1002/ajoc.202300113
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel threonine-derived amino sulfonamide organocatalysts were developed and applied to the asymmetric aldol reactions. The reactions of cyclohexanones with aromatic aldehydes catalyzed by the threonine-derived tosylamide provided anti-aldol adducts in good yield with high diastereo- and enantioselectivity. On the other hand, syn-aldol adducts were obtained in the reactions between alpha-siloxyacetone and aromatic aldehydes using threonine-derived triflamide catalyst. In both cases, a significant improvement in diastereoselectivity was observed compared to threonine-derived carboxylic acid catalyst.
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页数：5
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