In:
CHIMIA, Swiss Chemical Society, Vol. 61, No. 5 ( 2007-05-30), p. 269-
Abstract:
Bifunctional amino thiourea-catalyzed asymmetric additions of several nucleophiles into electron-deficient unsaturated compounds such as nitroolefins, ?,?-unsaturated imides, imines, and azodicarboxylates are described. We discovered that bifunctional thioureas bearing a
tertiary amino group significantly accelerated several nucleophilic addition reactions of active methylene compounds to electron-deficient double bonds. In these reactions, a strong hydrogen-bonding ability of the thiourea moiety as well as an appropriate Brønsted basicity of the tertiary amine is crucial for high enantioselectivity. This dual activation of both nucleophiles and electrophiles by the bifunctional thiourea expanded the applicability of the thiourea-catalyzed enantioselective reaction. In addition, these organocatalyzed asymmetric reactions were successfully applied
to the concise asymmetric synthesis of natural products and medicinal candidates such as epibatidine, baclofen, and CP-99,994.
Type of Medium:
Online Resource
ISSN:
2673-2424
,
0009-4293
DOI:
10.2533/chimia.2007.269
Language:
Unknown
Publisher:
Swiss Chemical Society
Publication Date:
2007
detail.hit.zdb_id:
2179192-2
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