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Citation: ZHANG He-Sheng, William Kitching. A Modified Synthesis of (R)-and(S)-(2-Benzyloxyethyl)oxirane from (S)-and (R)-Aspartic Acid[J]. Chinese Journal of Applied Chemistry, ;2002, 19(3): 304-306. shu

A Modified Synthesis of (R)-and(S)-(2-Benzyloxyethyl)oxirane from (S)-and (R)-Aspartic Acid

ZHANG He-Sheng ^a,b,, ,
William Kitching ^b

1.
a Faculty of Chemical and Material Science, Hubei University, Wuhan 430062;
2.
b Department of Chemistry, The University of Queensland, Brisbane, Qld4072, Australia

Corresponding author: ZHANG He-Sheng,
Received Date: 15 June 2001
Available Online: 4 December 2001

(R)-and (S)-(2-benzyloxyethyl)oxirane 1 were prepared from (S) and (R) aspartic acid by modification of the procedure described by Rapoport. Aspartic acid was converted into bromosuccinic acid 2 by treatment with sodium nitrite/potassium bromide/sulfuric acid,the diacid 2 was then reduced with freshly prepared boron trifluoride ethyl ether complex to bromodiol 3, which was further treated with sodium hydride and benzylbromide/TBAI(tetrabutylammonium iodide) to afford (2-benzyloxyethyl)oxirane. This procedure has shown the good yield, mild condition and excellent enantiomeric purity of the product.
- (benzyloxyethyl) oxirane,
- aspartic acid,
- asymmetric synthesis
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