Literature DB >> 19772285

Asymmetric carbon-carbon bond formation gamma to a carbonyl group: phosphine-catalyzed addition of nitromethane to allenes.

Sean W Smith1, Gregory C Fu.   

Abstract

A chiral phosphine catalyzes the addition of a carbon nucleophile to the gamma position of an electron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric gamma functionalization of carbonyl (and related) compounds.

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Year:  2009        PMID： 19772285      PMCID： PMC2758928          DOI： 10.1021/ja9061823

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


  11 in total

1.  Enantioselective Acylations Catalyzed by Chiral Phosphines.

Authors:  E. Vedejs; O. Daugulis; S. T. Diver
Journal:  J Org Chem       Date:  1996-01-26       Impact factor: 4.354

2.  Tandem reactions to construct heterocycles via phosphine-catalyzed umpolung addition and intramolecular conjugate addition.

Authors:  Cheng Lu; Xiyan Lu
Journal:  Org Lett       Date:  2002-12-26       Impact factor: 6.005

3.  Catalytic asymmetric synthesis of piperidine derivatives through the [4 + 2] annulation of imines with allenes.

Authors:  Ryan P Wurz; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-09-07       Impact factor: 15.419

Review 4.  Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents.

Authors:  Syuzanna R Harutyunyan; Tim den Hartog; Koen Geurts; Adriaan J Minnaard; Ben L Feringa
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

5.  Reactions of electron-deficient alkynes and allenes under phosphine catalysis.

Authors:  X Lu; C Zhang; Z Xu
Journal:  Acc Chem Res       Date:  2001-07       Impact factor: 22.384

6.  Synthesis of gamma,delta-didehydrohomoglutamates by the phosphine-catalyzed gamma-addition reaction to acetylenic esters

Authors: 
Journal:  J Org Chem       Date:  2000-06-02       Impact factor: 4.354

Review 7.  Catalytic, enantioselective, vinylogous aldol reactions.

Authors:  Scott E Denmark; John R Heemstra; Gregory L Beutner
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-25       Impact factor: 15.336

8.  Phosphine-catalyzed enantioselective synthesis of oxygen heterocycles.

Authors:  Ying Kit Chung; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Phosphine-catalyzed annulation of thioamides and 2-alkynoates: a new synthesis of thiazolines.

Authors:  Bing Liu; Roman Davis; Biren Joshi; Daniel W Reynolds
Journal:  J Org Chem       Date:  2002-06-28       Impact factor: 4.354

Review 10.  Phosphine-triggered synthesis of functionalized cyclic compounds.

Authors:  Long-Wu Ye; Jian Zhou; Yong Tang
Journal:  Chem Soc Rev       Date:  2008-03-26       Impact factor: 54.564
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  28 in total

1.  Phosphine-catalyzed β'-umpolung addition of nucleophiles to activated α-alkyl allenes.

Authors:  Tioga J Martin; Venus G Vakhshori; Yang S Tran; Ohyun Kwon
Journal:  Org Lett       Date:  2011-04-14       Impact factor: 6.005

2.  Stereoselective Syntheses of α,β-Unsaturated γ-Amino Esters Through Phosphine-Catalyzed γ-Umpolung Additions of Sulfonamides to γ-Substituted Allenoates.

Authors:  Qing-Fa Zhou; Kui Zhang; Ohyun Kwon
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  Alkenyl carbonyl derivatives in enantioselective redox relay Heck reactions: accessing α,β-unsaturated systems.

Authors:  Chun Zhang; Celine B Santiago; Lei Kou; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-06-04       Impact factor: 15.419

4.  Phosphine-catalyzed asymmetric additions of malonate esters to {gamma}-substituted allenoates and allenamides.

Authors:  Riccardo Sinisi; Jianwei Sun; Gregory C Fu
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-12       Impact factor: 11.205

5.  Phosphine-Mediated Iterative Arene Homologation Using Allenes.

Authors:  Kui Zhang; Lingchao Cai; Xing Jiang; Miguel A Garcia-Garibay; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2015-08-31       Impact factor: 15.419

Review 6.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

7.  Enantioselective Carbon-Sulfur Bond Formation: γ Additions of Aryl Thiols to Allenoates Catalyzed by a Chiral Phosphepine.

Authors:  Yuji Fujiwara; Jianwei Sun; Gregory C Fu
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

8.  Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement.

Authors:  Wen-Bo Liu; Noriko Okamoto; Eric J Alexy; Allen Y Hong; Kristy Tran; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-04-18       Impact factor: 15.419

9.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2013-12-25       Impact factor: 6.222

10.  Catalytic asymmetric C-N bond formation: phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates.

Authors:  Rylan J Lundgren; Ashraf Wilsily; Nicolas Marion; Cong Ma; Ying Kit Chung; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-21       Impact factor: 15.336
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