title: Highly enantioselective catalytic dynamic resolution of N-Boc-2-lithiopiperidine: synthesis of (R)-(+)-N-Boc-pipecolic acid, (S)-(-)-coniine, (S)-(+)-pelletierine, (+)-beta-conhydrine, and (S)-(-)-ropivacaine and formal synthesis of (-)-lasubine II and (+)-cermizine C.
abstract: The catalytic dynamic resolution (CDR) of rac-2-lithio-N-Boc-piperidine using chiral ligand 8 or its diastereomer 9 in the presence of TMEDA has led to the highly enantioselective syntheses of both enantiomers of 2-substituted piperidines using a wide range of electrophiles. The CDR has been applied to the synthesis of (R)- and (S)-pipecolic acid derivatives, (+)-beta-conhydrine, (S)-(+)-pelletierine, and (S)-(-)-ropivacaine and the formal synthesis of (-)-lasubine II and (+)-cermizine C.
authors.affiliation: Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA.
authors.forename: Timothy K
authors.initials: TK
authors.lastname: Beng
authors.forename: Robert E
authors.initials: RE
authors.lastname: Gawley
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D010875:Pipecolic Acids / Q000138:chemical synthesis / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry; D000077212:Ropivacaine; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000470:Alkaloids; D000577:Amides; D006574:Heterocyclic Compounds, 2-Ring; D009942:Organometallic Compounds; D010875:Pipecolic Acids; D010880:Piperidines; D011807:Quinolizines; C520251:alpha-conhydrine; C518697:cermizine C; C414385:lasubin I; C008195:isopelletierine; C032727:piperidine; D000077212:Ropivacaine; D008094:Lithium; C007112:coniine; C031345:pipecolic acid
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