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Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines.

Abstract:
A catalytic asymmetric synthesis of imidazolines with a fully substituted β-carbon atom by a Mannich-type addition/cyclization reaction of isocyanoacetate pronucleophiles and N-diphenylphosphinoyl ketimines has been developed. When a combination of a cinchona-derived aminophosphine precatalyst and silver oxide was employed as a binary catalyst system, good reactivity, high diastereoselectivities (up to 99:1 d.r.), and excellent enantioselectivities (up to 99% ee) were obtained for a range of substrates.
Publication status:
Published

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Publisher copy:
10.1002/anie.201309719

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Publisher:
Wiley
Journal:
Angewandte Chemie (International ed. in English)
Volume:
53
Issue:
13
Pages:
3462-3465
Publication date:
2014-03-01
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Source identifiers:
457856
Language:
English
Keywords:
Pubs id:
pubs:457856
UUID:
uuid:fc600183-3cc9-4642-9a4a-32ad4818e6e9
Local pid:
pubs:457856
Deposit date:
2014-05-18

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