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

作者：Arai Takayoshi^*; Yamamoto Yushi

来源：Organic Letters, 2014, 16(6): 1700-1703.

DOI：10.1021/ol500361w

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.

• 出版日期2014-3-21