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A Phosphane‐Mediated Diastereoselective, Domino aza ‐Morita–Baylis–Hillman/Reduction Sequence Involving Water as Hydrogen Source
Author(s) -
Duvvuru Deepti,
Retailleau Pascal,
Betzer JeanFrançois,
Marinetti Angela
Publication year - 2012
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.201101712
Subject(s) - chemistry , domino , adduct , nucleophile , sequence (biology) , morita therapy , hydrogen , reduction (mathematics) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry , psychology , geometry , mathematics , psychoanalysis
The new domino process disclosed here involves PBu 3 as both a nucleophilic and a reducing agent. The process combines suitable electron‐poor dienes, N ‐tosylimines, tri‐ n ‐butylphosphane and water. The final products formally result from reduction of vinylogous aza ‐Morita–Baylis–Hillman adducts. The reaction proceeds with an excellent stereochemical control of the relative configurations of the newly created contiguous carbon centres.