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Literature DB >> 19722664

Catalytic asymmetric synthesis of alpha-alkylidene-beta-hydroxy esters via dynamic kinetic asymmetric transformation involving Ba-catalyzed direct aldol reaction.

Akitake Yamaguchi¹, Shigeki Matsunaga, Masakatsu Shibasaki.

Abstract

A Ba-catalyzed dynamic kinetic asymmetric transformation (DYKAT) involving a direct aldol/retro-aldol reaction of beta,gamma-unsaturated ester donors is described. A Ba(O-iPr)(2)/BINOL complex promoted the direct aldol reaction/isomerization sequence, and alpha-alkylidene-beta-hydroxy esters were obtained from aryl, heteroaryl, alkenyl, and alkyl aldehydes under simple proton-transfer conditions with 99-87% ee and >20:1 to 15:1 alpha/gamma selectivity.

Entities: Chemical

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Year: 2009 PMID： 19722664 DOI： 10.1021/ja904575e

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

6 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. Catalytic asymmetric synthesis of CF₃-substituted tertiary propargylic alcohols via direct aldol reaction of α-N₃ amide.

Authors: Hidetoshi Noda; Fuyuki Amemiya; Karin Weidner; Naoya Kumagai; Masakatsu Shibasaki
Journal: Chem Sci Date: 2017-03-02 Impact factor: 9.825

3. Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts.

Authors: Dan Li; Yuling Yang; Minmin Zhang; Linqing Wang; Yingfan Xu; Dongxu Yang; Rui Wang
Journal: Nat Commun Date: 2020-05-22 Impact factor: 14.919

Catalytic asymmetric synthesis of alpha-alkylidene-beta-hydroxy esters via dynamic kinetic asymmetric transformation involving Ba-catalyzed direct aldol reaction.

Review 1. The direct catalytic asymmetric aldol reaction.

2. Catalytic asymmetric synthesis of CF₃-substituted tertiary propargylic alcohols via direct aldol reaction of α-N₃ amide.

3. Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts.

4. Managing the retro-pathway in direct catalytic asymmetric aldol reactions of thioamides.

5. 2,2'-[(1S,2S)-1,2-Bis(2-hy-droxy-phen-yl)ethane-1,2-di-yl]bis(isoindoline-1,3-dione) ethanol monosolvate hemihydrate.

6. Lewis acid-catalyzed asymmetric reactions of β,γ-unsaturated 2-acyl imidazoles.

Catalytic asymmetric synthesis of alpha-alkylidene-beta-hydroxy esters via dynamic kinetic asymmetric transformation involving Ba-catalyzed direct aldol reaction.

Review 1. The direct catalytic asymmetric aldol reaction.

2. Catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide.

3. Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts.

4. Managing the retro-pathway in direct catalytic asymmetric aldol reactions of thioamides.

5. 2,2'-[(1S,2S)-1,2-Bis(2-hy-droxy-phen-yl)ethane-1,2-di-yl]bis(isoindoline-1,3-dione) ethanol monosolvate hemihydrate.

6. Lewis acid-catalyzed asymmetric reactions of β,γ-unsaturated 2-acyl imidazoles.

2. Catalytic asymmetric synthesis of CF₃-substituted tertiary propargylic alcohols via direct aldol reaction of α-N₃ amide.