Literature DB >> 11890780

A novel chiral sulfonium yilde: highly enantioselective synthesis of vinylcyclopropanes.

Song Ye1, Zheng-Zheng Huang, Chun-An Xia, Yong Tang, Li-Xin Dai.   

Abstract

A newly designed chiral sulfonium allylide, generated in situ from the corresponding sulfonium salt in the presence of KOBu(t), reacted with alpha,beta-unsaturated esters, ketones, amides, and nitriles to afford trans-2-silylvinyl-trans-3-substituted cyclopropyl esters, ketones, amides, and nitriles with outstanding diastereoselectivity and excellent enantioselectivity in good to high yields. A mechanistic rationale is proposed.

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Year:  2002        PMID: 11890780     DOI: 10.1021/ja0172969

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


  5 in total

1.  Reactivity of (1-methoxycarbonylpentadienyl)iron(1+) cations with hydride, methyl, and nitrogen nucleophiles.

Authors:  Yuzhi Ma; Young K Yun; Julie Wondergem Nee Lukesh; Anobick Sar; Jayapal Reddy Gone; Sergey Lindeman; William A Donaldson
Journal:  Tetrahedron       Date:  2017-06-15       Impact factor: 2.457

2.  [(1S,2S,3R,4R)-3-Hydr-oxy-4,7,7-tri-methyl-bicyclo-[2.2.1]heptan-2-yl]methyl[(E)-3-(trimethyl-silyl)prop-2-enyl]selen-onium bromide.

Authors:  Hai-Yang Wang; Qiang Zhang; Yi-Zhi Li; Yuan Gui; Zhi-Zhen Huang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-07

3.  Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles.

Authors:  Jing-Wen Kang; Xiang Li; Fei-Yu Chen; Yuan Luo; Shu-Cang Zhang; Bin Kang; Cheng Peng; Xu Tian; Bo Han
Journal:  RSC Adv       Date:  2019-04-17       Impact factor: 4.036

4.  Construct indeno[1,2-b]oxepine or cis-cyclopropylacrylate by sulfur ylides.

Authors:  Qinfang Chen; Yihao Pan; Dongxin Zhao; Weiran Yang; Jing Zheng
Journal:  RSC Adv       Date:  2020-06-08       Impact factor: 3.361

5.  Direct cyclopropanation of activated N-heteroarenes via site- and stereoselective dearomative reactions.

Authors:  Jiyoun Lee; Donguk Ko; Hyunju Park; Eun Jeong Yoo
Journal:  Chem Sci       Date:  2020-01-10       Impact factor: 9.825

  5 in total

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