Phosphazene-Catalyzed Cascade Esterification/Stereoselective Aza-Michael Addition of Chiral β-Trifluoromethyl-α,β-unsaturated N -Acylated Oxazolidin-2-ones

被引：1

作者：

Racochote, Sasirome ^{[1
]}

Kuhakarn, Chutima ^{[1
,2
]}

Leowanawat, Pawaret ^{[1
,2
]}

Reutrakul, Vichai ^{[1
,2
]}

Soorukram, Darunee ^{[1
,2
]}

机构：

[1] Mahidol Univ, Fac Sci, Dept Chem, Rama 6 Rd, Bangkok 10400, Thailand

[2] Mahidol Univ, Fac Sci, Ctr Excellence Innovat Chem PERCH CIC, Rama 6 Rd, Bangkok 10400, Thailand

来源：

SYNLETT | 2025年 / 36卷 / 04期

关键词：

aza-Michael addition; oxa-Michael addition; esterification; phosphazene; trifluoromethyl group; cascade reaction; PARTIALLY-MODIFIED RETRO; SOLUTION/SOLID-PHASE SYNTHESIS; ASYMMETRIC CONJUGATE ADDITION; CARBON CENTER BEARING; ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; CONSTRUCTION; FLUORINE; 1,2-DIAMINES; DERIVATIVES;

D O I：

10.1055/a-2364-6119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Upon treatment of chiral beta-trifluoromethyl-alpha,beta-unsaturated N -acylated oxazolidin-2-ones with a range of alcohols using phosphazene base as a catalyst, the unexpected cascade esterification/stereoselective aza-Michael addition was observed. The reactions proceeded with high diastereoselectivities (up to >99:1) to give a series of enantioenriched aza-Michael addition products in good to high yields. The structure and stereochemistry of the representative aza-Michael adduct were confirmed by X-ray crystal structure analysis. The plausible mechanism was proposed on the basis of the experimental results.The synthetic transformations of chiral aza-Michael addition products were also demonstrated highlighting the synthetic application of the present work.

引用

页码：329 / 334

页数：6

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