Highly Stereoselective aza‐Baylis–Hillman Reactions of CF 3 ‐Sulfinylimines: Straightforward Access to α‐Methylene β‐CF 3  β‐Amino Acids | Zendy

Milcent Thierry | Zendy; Hao Jing | Zendy; Kawada Kosuke | Zendy; Soloshonok Vadim A. | Zendy; Ongeri Sandrine | Zendy; Crousse Benoit | Zendy

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Highly Stereoselective aza‐Baylis–Hillman Reactions of CF 3 ‐Sulfinylimines: Straightforward Access to α‐Methylene β‐CF 3 β‐Amino Acids

Author(s) -

Milcent Thierry,

Hao Jing,

Kawada Kosuke,

Soloshonok Vadim A.,

Ongeri Sandrine,

Crousse Benoit

Publication year - 2014

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.201402078

Subject(s) - chemistry , methylene , stereoselectivity , octane , michael reaction , stereochemistry , amino acid , baylis–hillman reaction , organocatalysis , dabco , catalysis , enantioselective synthesis , medicinal chemistry , combinatorial chemistry , organic chemistry , biochemistry

1,4‐Diazabicyclo[2.2.2]octane‐catalyzed asymmetric aza‐Baylis–Hillman (ABH) reaction of ( R )‐ N ‐ tert ‐butanesulfinyl‐(3,3,3)‐trifluoroacetaldimine with various Michael acceptors proceeds with exceptionally high rates and stereochemical outcome. This ABH approach provides convenient and practical access to previously unknown enantiomerically pure α‐methylene β‐CF 3 β‐amino esters/acids, forthright useable for peptide synthesis.

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