Dynamic kinetic resolution of N-acylhemiaminals was performed by enantioselective acylation of the hydroxy groups with chiral twisted amides. The stereoselectivity was reversed in the presence of 4-DMAP. The absolute configuration of the products was determined based on the sign of CD Cotton effects
โฆ LIBER โฆ
Kinetic resolution of sec-alcohols with axially chiral twisted amides
โ Scribed by Shinji Yamada; Takumi Ohe
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 210 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Kinetic resolution of sec-alcohols was performed by using axially chiral twisted amides, 4-(S)-alkyl 3-pivaloyl-l,3-thiazolidine-2-thiones (lb-ld and 2). The (S)-pivalates were selectively produced under neutral conditions; in contrast, the (R)-isomers were produced as major products in the presence of MeMgBr.
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