Literature DB >> 17764186

Highly enantioselective carbonyl-ene reactions catalyzed by a hindered silyl-salen-cobalt complex.

Gerri E Hutson1, Apurva H Dave, Viresh H Rawal.   

Abstract

We report here the enantioselective carbonyl-ene reactions of various 1,1-disubstituted and trisubstituted alkenes with ethyl glyoxylate. The reactions are catalyzed by a new Co-salen complex, in which bulky triisobutylsilyl (TIBS) substituents occupy the positions ortho to the phenolic oxygens. This complex catalyzes the reactions under nearly ideal conditions - at room temperature and using catalyst loadings as low as 0.1 mol % - and provides the chiral, homoallylic alcohol products in excellent yields, enantioselectivities, and diastereoselectivities.

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Year:  2007        PMID: 17764186     DOI: 10.1021/ol071342d

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


  7 in total

1.  Mechanistic basis for high reactivity of (salen)Co-OTs in the hydrolytic kinetic resolution of terminal epoxides.

Authors:  Lars P C Nielsen; Stephan J Zuend; David D Ford; Eric N Jacobsen
Journal:  J Org Chem       Date:  2012-02-08       Impact factor: 4.354

2.  Solvent enhancement of reaction selectivity: a unique property of cationic chiral dirhodium carboxamidates.

Authors:  Xiaochen Wang; Carolin Weigl; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2011-05-27       Impact factor: 15.419

3.  Mechanistic basis for high stereoselectivity and broad substrate scope in the (salen)Co(III)-catalyzed hydrolytic kinetic resolution.

Authors:  David D Ford; Lars P C Nielsen; Stephan J Zuend; Charles B Musgrave; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-10-07       Impact factor: 15.419

4.  Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters.

Authors:  Haruo Aikawa; Tetsuro Kaneko; Naoki Asao; Yoshinori Yamamoto
Journal:  Beilstein J Org Chem       Date:  2011-05-20       Impact factor: 2.883

5.  Lanthanide complexes combined with chiral salen ligands: application in the enantioselective epoxidation reaction of α,β-unsaturated ketones.

Authors:  Xuexiu Xia; Chengrong Lu; Bei Zhao; Yingming Yao
Journal:  RSC Adv       Date:  2019-05-03       Impact factor: 4.036

6.  Salen promoted enantioselective Nazarov cyclizations of activated and unactivated dienones.

Authors:  Gerri E Hutson; Yunus E Türkmen; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2013-03-25       Impact factor: 15.419

7.  F10BINOL-derived chiral phosphoric acid-catalyzed enantioselective carbonyl-ene reaction: theoretical elucidation of stereochemical outcomes.

Authors:  Jun Kikuchi; Hiromu Aramaki; Hiroshi Okamoto; Masahiro Terada
Journal:  Chem Sci       Date:  2018-11-19       Impact factor: 9.825

  7 in total

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