title: One-pot in situ formation and reaction of trimethyl(trichloromethyl)silane: application to the synthesis of 2,2,2-trichloromethylcarbinols.
abstract: 2,2,2-Trichloromethylcarbinols are 1 are valuable synthetic intermediates with a multitude of uses. A scalable procedure for the synthesis of TMS-protected-2,2,2-trichloromethylcarbinols and 2,2,2-trichloromethylcarbinols 1 was developed that employs the in situ generation and reaction of trimethyl(trichloromethyl)silane (CCl(3)-TMS). The procedure avoids the exposure of the carbonyl compounds to the strongly basic conditions typically used for this transformation and also avoids isolation of the difficult-to-handle CCl(3)-TMS. This procedure was applied to diastereoselective trichloromethyl additions to 2-substituted 4-piperidinones and to reactions with a variety of structurally diverse aldehydes and ketones.
authors.affiliation: Pfizer Global Research and Development, Groton Laboratories, Eastern Point Road, Groton, Connecticut 06340, USA. kevin.e.henegar@pfizer.com
authors.forename: Kevin E
authors.initials: KE
authors.lastname: Henegar
authors.forename: Ricardo
authors.initials: R
authors.lastname: Lira
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D000432:Methanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010881:Piperidones / Q000138:chemical synthesis / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D007659:Ketones; D010881:Piperidones; D014297:Trimethylsilyl Compounds; C520713:trichloromethyltrimethylsilane; D000432:Methanol