Enantioselective hydrogenation of 3-alkylidenelactams: high-throughput screening provides a surprising solution.
High-throughput screening of 256 potential catalysts (8 metal precursors x 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level.
Yue
Tai-Yuen
TY
Bristol-Myers Squibb Company, Process Research and Development Department, Chambers Works, P.O. Box 269, Deepwater, New Jersey 08023-0269, USA.
Nugent
William A
WA
D000466:Alkadienes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D006865:Hydrogenation; D007769:Lactams / Q000737:chemistry*; D010420:Pentanes / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
C470607:2,4-bis(diphenylphosphino)pentane; D000466:Alkadienes; D000475:Alkenes; D007769:Lactams; D010420:Pentanes; D010720:Phosphines; C439868:1,5-cyclooctadiene