Enantiocontrolled synthesis of 2,3,6-trisubstituted piperidines using (eta(3)-dihydropyridinyl)molybdenum complexes as chiral scaffolds. Total synthesis of (-)-indolizidine 209B.
Enantiopure TpMo(CO)2(pyridinyl) complexes were prepared using an efficient and scalable enzymatic kinetic resolution of the precursor to the molybdenum complex. A single TpMo(CO)2(pyridinyl) complex can function as a chiral scaffold for the enantiocontrolled synthesis of either 2,3,6-cis- or 2,6-cis-3-trans-trisubstituted piperidines. The synthetic potential of this methodology was demonstrated by a total synthesis of (-)-indolizidine 209B.
Shu
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Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, Georgia 30322, USA.
Alcudia
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A
Yin
J
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Liebeskind
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LS
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D001001:Anura; D018360:Crystallography, X-Ray; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D008982:Molybdenum / Q000737:chemistry*; D018733:Nicotinic Antagonists / Q000138:chemical synthesis / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007212:Indolizines; D018733:Nicotinic Antagonists; D009942:Organometallic Compounds; D010880:Piperidines; C445134:indolizidine 209B; D008982:Molybdenum