Open AccessO -nitroso aldol synthesis: Catalytic enantioselective route to α-aminooxy carbonyl compounds via enamine intermediate
Author(s) -
Norie Momiyama,
Hiromi Torii,
Susumu Saito,
Hisashi Yamamoto
Publication year - 2004
Publication title -
proceedings of the national academy of sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.0307785101
Subject(s) - enamine , enantioselective synthesis , pyrrolidine , chemistry , aldol reaction , catalysis , nitroso , tetrazole , substrate (aquarium) , organic chemistry , stereochemistry , combinatorial chemistry , oceanography , geology
The approach using pyrrolidine enamine as substrate has been studied for this synthesis, and an important catalyst structural feature has been developed. After survey of pyrrolidine-based Brønsted acid catalyst, tetrazole catalyst (3f) was found to be optimal in synthesis of aminooxy carbonyl compounds in high yields, with complete enantioselectivity not only for aldehydes but also for ketones.
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