Synthesis of Three-, Five-, and Six-Membered Heterocycles Derived from New β-Amino-α-(trifluoromethyl) Alcohols

被引：14

作者：

Obijalska, Emilia ^{[1
]}

Mloston, Grzegorz ^{[1
]}

Linden, Anthony ^{[2
]}

Heimgartner, Heinz ^{[2
]}

机构：

[1] Univ Lodz, Dept Organ & Appl Chem, PL-91403 Lodz, Poland

[2] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

来源：

HELVETICA CHIMICA ACTA | 2010年 / 93卷 / 09期

关键词：

TRIFLUOROMETHYL AZIRIDINES; ASYMMETRIC FLUORINATION; PERFLUOROALKYLATION; CARBON;

D O I：

10.1002/hlca.201000232

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nucleophilic trifluoromethylation of alpha-imino ketones 2, derived from arylglyoxal. with Ruppert-Prakash reagent (CF3SiMe3) offers a convenient access to the corresponding O-silylated beta-imino-alpha-(trifluoromethyl) alcohols. In a 'one-pot' procedure, by treatment with NaBH4, these products smoothly undergo reduction and desilylation yielding the expected beta-amino-alpha-(trifluoromethyl) alcohols 4. The latter were used as starting materials for the synthesis of diverse trifluoromethylated heterocycles, including aziridines 5, 1,3-oxazolidines 8, 1,3-oxazolidin-2-ones 9, 1,3,2-oxazaphospholidine 2-oxides 10, 1,2,3-oxathiazolidine 2-oxides 11, and morpholine-2,3-diones 12. An optically active 5-(trifluoromethyl)-substituted 1,3-oxazolidin-2-one 9g was also obtained.

引用

页码：1725 / 1736

页数：12

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