Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-Proline-Catalysed α-Aminooxylation

作者: Tanveer Mahamadali Shaikh , Arumugam Sudalai

DOI: 10.1002/EJOC.201000169

关键词:

摘要: An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)-α-conhydrine (98 % ee) and (-)-sedamine (95 ee), by L -proline-catalysed α-aminooxylation aldehydes has been developed. The strategy involves an intramolecular cyclization construct core.

参考文章(91)
Pavel Peĉ, Ŝárka Adámková, Ivo Frébort, Marek ŜEbela, Probing the active site of pea seedlings amine oxidase with optical antipodes of sedamine alkaloids. Journal of Enzyme Inhibition. ,vol. 16, pp. 367- 372 ,(2001) , 10.1080/14756360109162385
Pascal Laurent, Jean-Claude Braekman, Désiré Daloze, Enantioselective Syntheses and Absolute Configuration of the Ladybird Defence Alkaloids (+)‐Calvine and (+)‐2‐Epicalvine European Journal of Organic Chemistry. ,vol. 2000, pp. 2057- 2062 ,(2000) , 10.1002/1099-0690(200006)2000:11<2057::AID-EJOC2057>3.0.CO;2-F
Mallam Venkataiah, Nitin W. Fadnavis, A novel stereoselective synthesis of (−)-β-conhydrine from (R)-2,3-O-cyclohexylidine glyceraldehyde Tetrahedron. ,vol. 65, pp. 6950- 6952 ,(2009) , 10.1016/J.TET.2009.06.060
Yukio Masaki, Toshihiro Imaeda, Kinnosuke Nagata, Hirohisa Oda, Akichika Ito, Enantiospecific synthesis of optically active natural (+)-conhydrine from (S,S)-tartaric acid Tetrahedron Letters. ,vol. 30, pp. 6395- 6396 ,(1989) , 10.1016/S0040-4039(01)93904-8
Louis V. Adriaenssens, Carolyn A. Austin, Mairi Gibson, David Smith, Richard C. Hartley, Stereodivergent Diversity Oriented Synthesis of Piperidine Alkaloids European Journal of Organic Chemistry. ,vol. 2006, pp. 4998- 5001 ,(2006) , 10.1002/EJOC.200600744
Santos Fustero, Diego Jiménez, Javier Moscardó, Silvia Catalán, Carlos del Pozo, Enantioselective organocatalytic intramolecular aza-Michael reaction: a concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine. Organic Letters. ,vol. 9, pp. 5283- 5286 ,(2007) , 10.1021/OL702447Y
Roderick W. Bates, Kanicha Sa-Ei, Syntheses of the sedum and related alkaloids Tetrahedron. ,vol. 58, pp. 5957- 5978 ,(2002) , 10.1016/S0040-4020(02)00584-7
Nathan S. Josephsohn, Marc L. Snapper, Amir H. Hoveyda, Ag-catalyzed asymmetric mannich reactions of enol ethers with aryl, alkyl, alkenyl, and alkynyl imines. Journal of the American Chemical Society. ,vol. 126, pp. 3734- 3735 ,(2004) , 10.1021/JA049388E