Tetrahedron p. 3349 - 3362 (1994)
Update date:2022-08-04
Topics:
Enders, Dieter
Schaefer, Thomas
Piva, Olivier
Zamponi, Andrea
A practical and efficient enantioselective synthesis of 2-sulfenylated aldehydes (S)-6 is described, based on the α-alkylation of sulfenylated acetaldehyde SAMP hydrazones (S)-4, easily prepared from bromoacetaldehyde diethylacetal 1, thiols and (S)-1-amino-2-methoxymethyl-pyrrolidine (SAMP).A chemoselective oxidative cleavage of the intermediate SAMP hydrazones (S,S)-5 with ozone gives rise to the title compounds (S)-6 in good overall yields and high enantiomeric excess of up to 97percent.
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Doi:10.1021/ja00088a063
(1994)Doi:10.1021/jm00040a018
(1994)Doi:10.1021/acs.orglett.9b04068
(2019)Doi:10.1016/j.poly.2013.12.017
(2014)Doi:10.1016/0022-328X(94)80081-2
(1994)Doi:10.1134/S1070363213120116
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