- Enantioselective reduction of 2-keto-3-haloalkane phosphonates by Baker's yeast
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Bioreduction of 3-substituted-2-oxoalkanephosphonates by baker's yeast afforded 3-substituted-2-hydroxy-alkanephosphonates in moderate to good yields and ee value. These compounds could serve as useful chirons for the stereoselective synthesis of phosphorus analogs of biologically active molecules including R-(-)-3-trimethylammonium-2-hydroxypropanoic acid and R-(-)-3-trimethylammonium-2-hydroxypropanoic acid.
- Yuan, Cheng-Ye,Wang, Ke,Li, Zu-Yi
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p. 551 - 556
(2007/10/03)
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- P-H INTERNAL CARBENES. IV. FORMATION OF O,O-DIMETHYL-3-CHLORO-2-OXOPROPYLPHOSPHONATE
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In reactions of ω-polychloro-substituted diazoacetones with dimethyl phosphite catalyzed by copper acetyloacetonate, products of carbenoid P-H introduction are formed. Reduction of the chlorine atoms in them is brought about as a result of a copper-catalyzed Atherton-Todd reaction.
- Polozov, A. M.,Mustafin, A. Kh.
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p. 850 - 852
(2007/10/02)
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- INSERTION OF CARBENES INTO P-H BONDS. 5. SYNTHESIS OF NEW PHOSPHONATES AND PHOSPHINATES IN REACTIONS CATALYSED BY Cu, Pd, Rh, Ni COMPLEXES
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Cu(OTf)2 and Cu(acac)2 were found to be the most effective catalysts in the reaction of diazo compounds Ph2CN2 (1a), EtOC(O)CHN2 (1b), MeOC(O)CHN2 (1c), MeC(O)CN2C(O)OMe (1d), ClCH2C(O)CHN2 (1e) and CH2N2 (1f) with hydrophosphoryl compounds (MeO)2P(O)H (2a), (t-BuO)2P(O)H (2b), Ph(MeO)P(O)H (2c), (EtO)2P(O)H (2d) and P(O)H (2e) resulting in P-C bond formations.Cu, Pd and Rh acetates and Ni(acac)2 have a much lower efficiency.Chlorines in Cl3CC(O)CH2P(O)(OMe)2 (3k) and Cl2CHC(O)CH2P(O)(OMe)2 (3l) are reduced in the copper catalysed Atherton-Todd reaction.Key words: Catalyst; diazo compound; hydrophosphoryl compound; insertion; phosphonate; phosphinate.
- Polozov, Alexander M.,Mustaphin, Albert H.,Khotinen, Alexander V.
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p. 153 - 160
(2007/10/02)
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