상세 정보

underline
Metadata Downloads : dc(xml) or Excel
Cited 0 time in scopus ci

Title 

Highly diastereoselective epimerization: stereodivergent synthesis of α-hydroxy-β-amino isopentanoic acid

 

알파-히드록시-베타-아미노 이소펜탄오익 에시드의 입체선택적인 합성

Authors 

W D SeoM J Curtis-LongYoung Bae RyuJ H LeeM S YangWoo Song LeeK H Park

Publisher 

American Chemical Society

Issue Date 

2006

Citation 

Journal of Organic Chemistry, vol. 71, no. 13, pp. 5008-5011

Keywords 

synthesis (chemical)α-hydroxy-β-amino isopentanoic acidepimerizationamino acidsalpha hydroxy beta aminoisopentanoic acidcarboxylic acid derivativevaleric acid derivative

Abstract 

The high diastereoselectivity of the base-catalyzed epimerization of oxazolidin-2-ones 7 and 8 is shown to depend on the nature of the N-substituent (R group); when R = Bn, the 4,5-trans-product (4S,5R)-9 is formed, whereas when R = H the 4,5-cis-product (45,55)-10 is formed, both with >99:1 dr. The successful hydrolysis of the oxazolidin-2-one group in both cis- and trans-derivatives show this to be a stereodivergent route to enantiopure α-hydroxy-β-amino isopentanoic acids (2R,3S)-1 and (25,35)-2.

ISSN 

0022-3263

Link 

http://dx.doi.org/10.1021/jo060309m

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2019-05-02


There are no files associated with this item.
qrcode

FusionCharts.
DSpace Software Coptright(c) 2010 MIT and Hewleft-Packard  /  KRIBB-REPOSITORY ( Email:jakim@kribb.re.kr)