Asymmetric synthesis of chiral beta-amiNo acids

Details Asymmetric synthesis of chiral beta-amiNo acids Asymmetric synthesis of chiral beta-amiNo acids

1997-07-10

1998-11-24

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

546329, 549494, 560 39, 560 35, 556413, 556418, C07C22900

Patent

active

058409610

ABSTRACT:
The invention herein is directed to a process for the preparation of ethyl 3S-amino-4-pentynoate which involves treating 3-(trimethylsilyl)-2-propynal with L-phenylglycinol in toluene to produce with BrZnCH.sub.2 CO.sub.2 t-Bu in THF/NMP to produce 1,1-dimethylethyl reacting the 1,1-dimethylethyl sodium periodate to form 1,1-dimethylethyl 1,1-dimethylethyl 1,1-dimethylethyl 3S-amino-5-(trimethylsilyl)-4-pentynoate; transesterifying 1,1-dimethyl 3S-amino-5-(trimethylsilyl)-4-pentynoate and desilylating to produce ethyl 3S-amino-4-pentynoate.

REFERENCES:
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patent: 5631399 (1997-05-01), Babiak et al.
Hua et al. "Synthesis of 4-Substituted 2-Azetidinones", Tetrahedron Letters, vol. 26, No. 5, pp. 548-550, (1985).
Tetsuji Kametani "Synthesis of Carbapenem Antibiotics," Heterocycles, vol. 17, 463-506, (1982).
Andres et al. "Stereoselective Ring Opening of Chiral Oxazolidines by Reformatsky Reagents: An Enantioselective Entry to .beta.-Amino Esters," Tetrahedron Letters, vol. 33, 2895-2898, (1992).
Mokhallalati et al. "An Efficient Enantiomeric Three Step Synthesis of .beta.-Amino Acids (Esters )" Tetrahedron Letters, vol. 34, No. 1, pp. 47-50, 1993.

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