Publication:
Highly diastereoselective alkylation of vicinal dianions of chiral succinic acid derivatives: A new general strategy to (R)-β-arylmethyl-γ- butyrolactones

Issued Date

2004-05-24

Resource Type

Article

ISSN

00404039

DOI

10.1016/j.tetlet.2004.04.008

Other identifier(s)

2-s2.0-2342498603

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron Letters. Vol.45, No.22 (2004), 4315-4318

Suggested Citation

Manat Pohmakotr, Darunee Soorukram, Patoomratana Tuchinda, Samran Prabpai, Palangpon Kongsaeree, Vichai Reutrakul Highly diastereoselective alkylation of vicinal dianions of chiral succinic acid derivatives: A new general strategy to (R)-β-arylmethyl-γ- butyrolactones. Tetrahedron Letters. Vol.45, No.22 (2004), 4315-4318. doi:10.1016/j.tetlet.2004.04.008 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/21185

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Title

Highly diastereoselective alkylation of vicinal dianions of chiral succinic acid derivatives: A new general strategy to (R)-β-arylmethyl-γ- butyrolactones

Author(s)

Manat Pohmakotr
 Darunee Soorukram
 Patoomratana Tuchinda
 Samran Prabpai
 Palangpon Kongsaeree
 Vichai Reutrakul

Other Contributor(s)

Mahidol University

Abstract

The vicinal dianions derived from chiral succinic acid derivatives, 1,4-bis[(4R,5S)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl]butane-1,4-dione and 1,4-bis[(4S,5R)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl]butane-1,4- dione react with arylmethyl bromides with high diastereo- and regio-selectivity to provide the corresponding chiral α-arylmethylated succinic acid derivatives; the (R)-products are converted into (R)-β-arylmethyl-γ- butyrolactones and (R)-α-arylmethyl-γ-butyrolactones. © 2004 Elsevier Ltd. All rights reserved.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/21185

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Scopus 2001-2005