American Chemical Society
ol500361w_si_002.cif (542.85 kB)

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

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posted on 2014-03-21, 00:00 authored by Takayoshi Arai, Yushi Yamamoto
The (S,S)-diphenylethylenediamine-derived imidazoline–aminophenol–Ni complex catalyzed tandem asymmetric Michael/Henry reaction of 2-mercaptobenzaldehydes with β-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 strereoselectivity.