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Literature DB >> 16235968

A practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center.

Osamu Tokuda¹, Taichi Kano, Wei-Guo Gao, Tetsuya Ikemoto, Keiji Maruoka.

Abstract

[reaction: see text] A concise and enantioselective synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid as a key intermediate for (S)-oxybutynin is reported. The crucial asymmetric tetrasubstituted carbon center was constructed with excellent stereoselectivity through the proline-catalyzed direct asymmetric aldol reaction between cyclohexanone and ethyl phenylglyoxylate under mild conditions.

Entities: Chemical

Mesh：

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Year: 2005 PMID： 16235968 DOI： 10.1021/ol052164w

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

10 in total

Review 1. The direct catalytic asymmetric aldol reaction.

Authors: Barry M Trost; Cheyenne S Brindle
Journal: Chem Soc Rev Date: 2010-02-17 Impact factor: 54.564

2. Organocatalytic enantioselective synthesis of alpha-hydroxy phosphonates.

Authors: Sampak Samanta; Cong-Gui Zhao
Journal: J Am Chem Soc Date: 2006-06-14 Impact factor: 15.419

Review 3. Enantioselective Tsuji allylations.

Authors: Justin T Mohr; Brian M Stoltz
Journal: Chem Asian J Date: 2007-12-03

4. Enantioselective synthesis of alpha-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates.

Authors: Barry M Trost; Jiayi Xu; Markus Reichle
Journal: J Am Chem Soc Date: 2007-01-17 Impact factor: 15.419

10. Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.

Authors: Qiang Sha; Hadi Arman; Michael P Doyle
Journal: Chem Commun (Camb) Date: 2016-01-04 Impact factor: 6.222

10 in total

A practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center.

Review 1. The direct catalytic asymmetric aldol reaction.

2. Organocatalytic enantioselective synthesis of alpha-hydroxy phosphonates.

Review 3. Enantioselective Tsuji allylations.

4. Enantioselective synthesis of alpha-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates.

5. CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications.

6. Developing novel organocatalyzed aldol reactions for the enantioselective synthesis of biologically active molecules.

7. Organocatalytic highly enantioselective synthesis of secondary alpha-hydroxyphosphonates.

8. Organocatalyzed enantioselective aldol reaction of 1H-pyrrole-2,3-diones.

9. Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.

10. Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.