Diversity-Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline-Aminophenol-Nickel-Catalyzed Michael/Henry Reaction

被引：47

作者：

Arai, Takayoshi ^{[1
]}

Yamamoto, Yushi ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 06期

关键词：

SELECTIVE 3+2 CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; CONTIGUOUS STEREOCENTERS; ALDOL REACTIONS; STEREOSELECTIVE-SYNTHESIS; DOMINO SYNTHESIS; ACCESS; CYCLOHEXANES; CONSTRUCTION; DERIVATIVES;

D O I：

10.1021/ol500361w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The (S,S)-diphenylethylenediamine-derived imidazoline-aminophenol-Ni complex catalyzed tandem asymmetric Michael/Henry reaction of 2-mercaptobenzaldehydes with beta-nitrostyrenes to give the corresponding (2S,3R,4R)-2-aryl-3-nitrothiochroman-4-ols in up to 99% diastereoselectivity with 95% ee was demonstrated in diversity-oriented asymmetric catalysis. Reduction of the nitro group of the chiral thiochromanes gave a new series of (2S,3R,4R)-3-amino-2-arylthiochroman-4-ols with retention of the strereoselectiyity.

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页码：1700 / 1703

页数：4

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