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

✍ Scribed by Emilia Obijalska; Grzegorz Mlostoń; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
269 KB
Volume
93
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Nucleophilic trifluoromethylation of α‐imino ketones 2, derived from arylglyoxal, with Ruppert–Prakash reagent (CF~3~SiMe~3~) offers a convenient access to the corresponding O‐silylated β‐imino‐α‐(trifluoromethyl) alcohols. In a ‘one‐pot’ procedure, by treatment with NaBH~4~, these products smoothly undergo reduction and desilylation yielding the expected β‐amino‐α‐(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.

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ChemInform Abstract: Synthesis of Three-
ChemInform Abstract: Synthesis of Three-, Five-, and Six-Membered Heterocycles Derived from New β-Amino-α-(trifluoromethyl) Alcohols.
✍ Emilia Obijalska; Grzegorz Mloston; Anthony Linden; Heinz Heimgartner 📂 Article 📅 2011 🏛 John Wiley and Sons ⚖ 46 KB 👁 1 views

## Abstract Trifluoromethylated β‐amino alcohols (I) are convenient starting compounds for the synthesis of a variety of trifluoromethylated three‐, five‐ and six‐membered heterocycles.