Literature DB >> 21142190

Asymmetric synthesis of tertiary benzylic alcohols.

Monika I Antczak1, Feng Cai, Joseph M Ready.   

Abstract

Vinyl, aryl, and alkynyl organometallics add to ketones containing a stereogenic sulfoxide. Tertiary alcohols are generated in diastereomerically and enantiomerically pure form. Reductive lithiation converts the sulfoxide into a variety of useful functional groups.

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Year:  2010        PMID: 21142190      PMCID: PMC3028934          DOI: 10.1021/ol102567h

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


  20 in total

1.  Development of bifunctional salen catalysts: rapid, chemoselective alkylations of alpha-ketoesters.

Authors:  Erin F DiMauro; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2002-10-30       Impact factor: 15.419

2.  Full chirality transfer in the conversion of secondary alcohols into tertiary boronic esters and alcohols using lithiation-borylation reactions.

Authors:  Viktor Bagutski; Rosalind M French; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-12       Impact factor: 15.336

3.  Highly active chiral phosphoramide-Zn(II) complexes as conjugate acid-base catalysts for enantioselective organozinc addition to ketones.

Authors:  Manabu Hatano; Takashi Miyamoto; Kazuaki Ishihara
Journal:  Org Lett       Date:  2007-09-29       Impact factor: 6.005

4.  Catalytic asymmetric alkylation of aldehydes with grignard reagents.

Authors:  Yusuke Muramatsu; Toshiro Harada
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 5.  Catalytic asymmetric organozinc additions to carbonyl compounds.

Authors:  L Pu; H B Yu
Journal:  Chem Rev       Date:  2001-03       Impact factor: 60.622

6.  Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones.

Authors:  Sang-Jin Jeon; Hongmei Li; Celina García; Lynne K LaRochelle; Patrick J Walsh
Journal:  J Org Chem       Date:  2005-01-21       Impact factor: 4.354

7.  Highly enantioselective phenylacetylene additions to ketones catalyzed by (S)-BINOL-Ti complex.

Authors:  Yifeng Zhou; Rui Wang; Zhaoqing Xu; Wenjin Yan; Lei Liu; Yongfeng Kang; Zhijian Han
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

8.  Highly enantioselective alkynylation of alpha-keto ester: an efficient method for constructing a chiral tertiary carbon center.

Authors:  Biao Jiang; Zili Chen; Xiaoxia Tang
Journal:  Org Lett       Date:  2002-10-03       Impact factor: 6.005

9.  Remote stereocontrol mediated by a sulfinyl group: synthesis of allylic alcohols via chemoselective and diastereoselective reduction of gamma-methylene delta-ketosulfoxides.

Authors:  José L García Ruano; M Angeles Fernández-Ibáñez; José A Fernández-Salas; M Carmen Maestro; Pablo Márquez-López; M Mercedes Rodríguez-Fernández
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

10.  Catalytic asymmetric generation of (Z)-disubstituted allylic alcohols.

Authors:  Luca Salvi; Sang-Jin Jeon; Ethan L Fisher; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2007-12-04       Impact factor: 15.419

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  2 in total

1.  Chiral allene-containing phosphines in asymmetric catalysis.

Authors:  Feng Cai; Xiaotao Pu; Xiangbing Qi; Vincent Lynch; Akella Radha; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2011-10-21       Impact factor: 15.419

2.  Straightforward Access to Thiocyanates via Dealkylative Cyanation of Sulfoxides.

Authors:  Uroš Todorović; Immo Klose; Nuno Maulide
Journal:  Org Lett       Date:  2021-03-16       Impact factor: 6.005

  2 in total

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