Tetrahedron p. 3073 - 3082 (1997)
Update date:2022-08-04
Topics:
Obika, Satoshi
Nishiyama, Toshihiko
Tatematsu, Satoshi
Miyashita, Kazuyuki
Imanishi, Takeshi
In the reduction of ketones with NADH mimics, (S(S))-1-substituted 3-(p-tolylsulfinyl)-1,4-dihydropyridines 1, the stereospecific transfer of one of the C-4 hydrogens, which is syn to the S-O bond, was experimentally revealed to be involved by employing the 2-methyl derivative 2 and the 4-deuterated derivatives 3a and 3b. The transition state model of this reaction was also proposed by consideration of the results obtained.
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