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Volumn 36, Issue 36, 1995, Pages 6449-6452

Enantioselective preparation of α-acyloxy ketones from α-hydroxy and α-amino acids

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029127912 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(95)01289-T Document Type: Article

Times cited : (32)

References (32)

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- For instance, the enantioselective oxidation of enolates (Davis, F. A.; Sheppard, A. C.; Lal, G. S. Tetrahedron Lett. 1989, 30, 779–782 and references cited herein, see also ref. 4b), the enantioselective mono-reduction of α-diones ( Chenevert, R.; Thiboutot, S. Chem. Lett. 1988, 1191–1192 and references cited herein), the oxidation of chiral propargylic alcohols (Miocque, M.; Hung, N. M.; Yen, V. Q. Ann. Chim., Paris) 1963, 8, 157–174) and the enantioselective acylation of chiral α-acyloxy stannanes by carboxylic acid chlorides ( Ye, J.; Bhapt, R. K.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 1–5).

11
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22
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- No isomerisation occurs during the preparation of the α-acyloxy acid chlorides described in Table 2 from the corresponding α-hydroxy acids. The pure carboxylic acid chlorides can be stored at 0–5°C and used within one month.

25
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28
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- The enantioselective mono-reduction of α-ketoacids (for instance, see Brown, H. C.: Pai, G. G.; Jadhav, P. K. J. Am. Chem. Soc. 1984, 106, 1531 and references cited herein), the 1,2-addition of organometallic reagents to chiral α-ketoesters (Boireau, G.; Deberly, A.;Abenhaïm, D. Tetrahedron Lett. 1989, 45, 5837–5840), the enantioselective oxidation and alkylation of metal enolates (Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437–2440 and references cited herein. Evans, D. A.; Morissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346–4348 and references cited herein. Fráter, Gy.; Müller, U.; Günther, W. Tetrahedron Lett. 1981, 22, 4221–4224), the oxidation of chiral propargylic alcohols (Midland, M.; Lee, P. E. J. Org. Chem. 1981, 46, 3933–3934.) or the enzymatic reduction of α-ketoacids, Kim, M. J.; Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 2959–2964 [[Truncated]]

29
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30
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- Mosandl¹ Gessner² Günther³ Deger⁴ Singer⁵

31
- 84915401025
- 1 mole of (L)-lactic acid as a 20% aqueous solution (Fluka 69782) was added to 11 of AcOH. Water was then removed by slow azeotropic distillation with a 20 cm fractionation column and the resulting solution of lactic acid in AcOH (ca 300 ml) was then added dropwise to an excess of acetyl chloride (2 moles). After stirring for 2 h at room temperature, the (S)-acetoxy propionic acid was isolated by distillation (100°C/0,01 torr). It was then added to 1.5 eq. of thionyl chloride in the presence of 1% DMF. After stirring for 2h, the (S)-acetoxy propionic acid chloride was isolated by distillation (53°C/ 10 torr) in 82% yield from lactic acid.

32
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