Literature DB >> 19237559

Alpha-fluoro-alpha-nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: efficient stereoselective Michael addition to chalcones.

G K Surya Prakash1, Fang Wang, Timothy Stewart, Thomas Mathew, George A Olah.   

Abstract

Highly efficient stereoselective 1,4-addition of racemic alpha-fluoro-alpha-nitro(phenylsulfonyl)methane (FNSM) as a fluoromethyl pronucleophile to alpha,beta-unsaturated ketones using a wide range of chiral organobifunctional catalysts under moderate conditions in the absence of an additional base has been achieved. A series of catalysts was screened for the enantioselective addition of FNSM to chalcones and the catalysts CN I, CD I, QN I-IV, and QD I were found to enable this reaction, successfully providing exclusive 1,4-addition products stereoselectively in high yields (conversion, diastereomeric ratio, and enantiomeric excess). Studies involving a model reaction and systematic analysis of the absolute configuration support the suggested mechanism.

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Year:  2009        PMID： 19237559      PMCID： PMC2657402          DOI： 10.1073/pnas.0900179106

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  22 in total

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Authors:  Tatsuya Furukawa; Norio Shibata; Satoshi Mizuta; Shuichi Nakamura; Takeshi Toru; Motoo Shiro
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4.  Irreversible inactivation of pig brain gamma-aminobutyric acid-alpha-ketoglutarate transaminase by 4-amino-5-halopentanoic acids.

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Authors:  Mark S Taylor; David N Zalatan; Andreas M Lerchner; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

6.  Stereoselective synthesis of trifluoromethylated vicinal ethylenediamines with alpha-amino N-tert-butanesulfinimines and TMSCF3.

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7.  Difluoromethyl phenyl sulfone as a selective difluoromethylene dianion equivalent: one-pot stereoselective synthesis of anti-2,2-difluoropropane-1,3-diols.

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8.  Irreversible inhibition of glutamate decarboxylase by alpha-(fluoromethyl)glutamic acid.

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Journal:  Biochemistry       Date:  1981-02-03       Impact factor: 3.162

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Authors:  Noriyuki Yamagiwa; Shigeki Matsunaga; Masakatsu Shibasaki
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10.  Efficient 1,4-addition of alpha-substituted fluoro(phenylsulfonyl)methane derivatives to alpha,beta-unsaturated compounds.

Authors:  G K Surya Prakash; Xiaoming Zhao; Sujith Chacko; Fang Wang; Habiba Vaghoo; George A Olah
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  3 in total

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Journal:  J Am Chem Soc       Date:  2016-10-17       Impact factor: 15.419

2.  Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter.

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3.  One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones.

Authors:  Xin Huang; Weizhao Zhao; Xiaofeng Zhang; Miao Liu; Stanley N S Vasconcelos; Wei Zhang
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  3 in total

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