- ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY PURE S-ISOSERINE
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KF-promoted addition of nitromethane on (-)-8-phenylmethyl glyoxylate monohydrate affords, after one purification, optically pure (-)S isoserine in about 50percent yield.
- Solladie-Cavallo, A.,Khiar, N.
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- C- and N-Selective Grignard Addition Reactions of α-Aldimino Esters in the Presence or Absence of Zinc(II) Chloride: Synthetic Applications to Optically Active Azacycles
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Highly practical synthetic methods were developed for the C- and N-selective Grignard addition reactions of N-4-MeOC6H4-protected α-aldimino esters in the presence or absence of zinc(II) chloride. Diastereoselective C-alkyl addition, tandem C-alkyl addition-N-alkylation, and some transformations to synthetically useful optically active azacycles were demonstrated. (Chemical Equation Presented).
- Hatano, Manabu,Yamashita, Kenji,Ishihara, Kazuaki
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supporting information
p. 2412 - 2415
(2015/05/27)
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- PREPARATION OF THREE DIASTEREOISOMERS OF 2-(1-METHYL-1-PHENYLETHYL)-5-METHYLCYCLOHEXAN-1-OL FROM (R)-(+)-PULEGONE
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New isolation of (1R,2S,5R)-(-)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexan-1-ol ((-)-8-phenylmenthol, Ia), prepared from (R)-(+)-pulegone, is described.The method consists in the preparation of phenylcarbamate of Ia and its transesterification with ethanol.Further two diastereoisomers of (-)-8-phenylmenthol were isolated: the (1S,2R,5R)-isomer IIa and the (1R,2R,5R)-isomer IIIa.Compounds Ia, IIa and IIIa were converted into their respective glyoxylates Ic, IIc and IIIc.
- Cervinka, Otakar,Svatos, Ales,Masojidkova, Milena
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p. 491 - 498
(2007/10/02)
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- ASYMMETRIC INDUCTION IN THE ENE REACTION OF GLYOXYLATE ESTERS OF 8-PHENYLMENTHOL
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We recently communicated (J.K.Whitesell, A.Bhattacharya, D.A.Aguilar and K.Henke, J.Chem.Soc.Chem.Commun. 989 (1982)) a highly efficient and effective method for the control of absolute stereochemistry through asymmetric induction in the ene reaction the chiral glyoxylate 1 with alkenes.We now have accumulated sufficient information on this process in terms of both its mechanistic details as well as its scope and applicability to a variety of situations that warrants a more complete presentation of these reactions.
- Whitesell, James K.,Bhattacharya, Apurba,Buchanan, Charles M.,Chen, H. H.,Deyo, Don,et al.
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p. 2993 - 3002
(2007/10/02)
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