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Tropos Biphenol Derived Chiral Thiophosphoramide Catalysed Highly Diastereo‐ and Enantioselective Michael Addition of Cyclic Ketones to Nitro Olefins
Author(s) -
Lu Aidang,
Wu Ronghua,
Wang Youming,
Zhou Zhenghong,
Wu Guiping,
Fang Jianxin,
Tang Chuchi
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000892
Subject(s) - chemistry , enantioselective synthesis , diastereomer , michael reaction , cyclohexanone , bifunctional , organocatalysis , chirality (physics) , nitro , aryl , pyrrolidine , transfer hydrogenation , alkyl , organic chemistry , stereochemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model , ruthenium
Chirality transfer from ( S )‐2‐(aminomethyl)pyrrolidine to the tropos biphenyl skeleton has been observed in the preparation of a chirally flexible biphenol‐derived novel chiral thiophosphoramide to afford exclusively the thermodynamically favoured diastereomer. This novel secondary amine–thiophosphoramide has proven to be an effective bifunctional organocatalyst for the asymmetric Michael addition of cyclohexanone to both aryl‐ and alkyl‐substituted nitro olefins. The corresponding adducts were obtained with excellent diastereo‐ (up to >99:1 dr ) and enantioselectivities (up to >99 % ee ).