Synthetic applicability and in situ recycling of a B-methoxy oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol.
A procedure is described that greatly simplifies the use of an oxazaborolidine catalyst derived from (1R,2S) cis-1-amino-indan-2-ol. This B-OMe catalyst has been employed in the asymmetric reduction of a number of structurally diverse prochiral ketones, in particular the reduction of alpha-amino acetophenone and its derivatives. A method for reducing the effective catalyst loading by "in situ recycling" is also presented. [structure: see text]
Gilmore
Nathan J
NJ
Department of Chemistry, Dainton Building, University of Sheffield, Sheffield, Brook Hill, Sheffield S3 7HF, UK.
Jones
Simon
S
Muldowney
Mark P
MP
D000605:Amino Alcohols / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D007189:Indans / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D010084:Oxidation-Reduction
D000605:Amino Alcohols; D001372:Aza Compounds; D001896:Boron Compounds; D007189:Indans; D007659:Ketones; C116915:aminoindanol; C496870:methoxy oxazaborolidine