New NADH models bearing a phosphonate or a chiral oxazaphospholidine oxide at the dihydropyridine ring

作者: Jean-Luc Vasse , Sophie Goumain , Vincent Levacher , Georges Dupas , Guy Quéguiner

DOI: 10.1016/S0040-4039(01)00027-2

关键词: OxideChemistryKetoneCombinatorial chemistryStereochemistryRing (chemistry)Bearing (mechanical)PhosphonateDihydropyridine

摘要: Abstract Novel NADH models bearing a phosphonate at the 3-position of stable 1,4-dihydroquinoline structure were successfully involved in reduction methyl benzoylformate. Asymmetric former ketone with model chiral oxazaphospholidine oxide is reported affording benzoylformate 45% e.e.

参考文章(15)
Atsuyoshi Ohno, Takahide Kimura, Hiroyuki Yamamoto, Seung Geon Kim, Shinzaburo Oka, Yutaka Ohnishi, Reduction by a Model of NAD(P)H. XIV. Mechanistic Consideration on the Role of Metal Ion Bulletin of the Chemical Society of Japan. ,vol. 50, pp. 1535- 1538 ,(1977) , 10.1246/BCSJ.50.1535
Vicky A. Burgess, Stephen G. Davies, Renato T. Skerlj, NADH mimics for the stereoselective reduction of benzoylformates to the corresponding mandelates. Tetrahedron-asymmetry. ,vol. 2, pp. 299- 328 ,(1991) , 10.1016/S0957-4166(00)82109-6
Satoshi Obika, Toshihiko Nishiyama, Satoshi Tatematsu, Kazuyuki Miyashita, Chuzo Iwata, Takeshi Imanishi, Studies on novel and chiral 1,4-dihydropyridines. III. Asymmetric reduction of some ketones with novel NADH model compounds, (SS)-3-(p-Tolylsulfinyl)-1,4-dihydropyridines Tetrahedron. ,vol. 53, pp. 593- 602 ,(1997) , 10.1016/S0040-4020(96)01005-8
Atsuyosi Ohno, Hiroyuki Yamamoto, Tadashi Okamoto, Shinzaburo Oka, Yutaka Ohnishi, Reduction by a Model of NAD(P)H. XV. Kinetics for the Reduction of Methyl Benzoylformate Bulletin of the Chemical Society of Japan. ,vol. 50, pp. 2385- 2386 ,(1977) , 10.1246/BCSJ.50.2385
Yves Combret, Jack Duflos, Georges Dupas, Jean Bourguignon, Guy Quéguiner, An approach to features responsible for the obtention of high e.e. with a highly enantioselective NADH model Tetrahedron. ,vol. 49, pp. 5237- 5246 ,(1993) , 10.1016/S0040-4020(01)82373-5
Sten Henriksson, Jan Sandström, THE RELATIVE DONOR CAPACITIES OF CH3 O AND CH3S BY ROTATIONAL BARRIER MEASUREMENTS Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 6, pp. 127- 127 ,(1979) , 10.1080/03086647908080337
Atsuyoshi Ohno, Satoshi Ushida, Mechanistic Models of Asymmetric Reductions ,(1986)
Jean Bourguignon, Georges Dupas, Vincent Levacher, Guy Quéguiner, Chiral NADH Models Derived from Optically Active Amino Alcohols Heterocycles. ,vol. 39, pp. 405- ,(1994) , 10.3987/REV-94-SR(B)2