Literature DB >> 21542622

Enantioselective dichlorination of allylic alcohols.

K C Nicolaou1, Nicholas L Simmons, Yongcheng Ying, Philipp M Heretsch, Jason S Chen.   

Abstract

The development of an enantioselective allylic alcohol dichlorination catalyzed by dimeric cinchona alkaloid derivatives and employing aryl iododichlorides as chlorine sources is reported. Reaction optimization, exploration of the substrate scope, and a model for stereoinduction are presented.
© 2011 American Chemical Society

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Year:  2011        PMID: 21542622      PMCID: PMC3107004          DOI: 10.1021/ja202555m

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


  29 in total

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5.  On the absolute configurational stability of bromonium and chloronium ions.

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Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

6.  Microbial sulpholipids: (R)-13-choro-1-(R)-14-docosanediol disulphate and polychlorosulpholipids in Ochromonas danica.

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Journal:  Biochem J       Date:  1969-07       Impact factor: 3.857

7.  Catalytic, asymmetric alpha-chlorination of acid halides.

Authors:  Stefan France; Harald Wack; Andrew E Taggi; Ahmed M Hafez; Ty R Wagerle; Meha H Shah; Crystal L Dusich; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2004-04-07       Impact factor: 15.419

8.  Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids.

Authors:  Grant M Shibuya; Jacob S Kanady; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2008-08-22       Impact factor: 15.419

9.  DABCO-catalyzed 1,4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene.

Authors:  Wen Zhang; Huadong Xu; Hui Xu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

10.  Enantioselective total synthesis of (-)-napyradiomycin A1 via asymmetric chlorination of an isolated olefin.

Authors:  Scott A Snyder; Zhen-Yu Tang; Ritu Gupta
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419

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  33 in total

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Authors:  Bradley B Gilbert; Stanley T-C Eey; Pavel Ryabchuk; Olivia Garry; Scott E Denmark
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2.  Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

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Journal:  J Am Chem Soc       Date:  2011-08-18       Impact factor: 15.419

3.  Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

Authors:  Susumu Oda; Hisashi Yamamoto
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4.  Approaches to the chemical synthesis of the chlorosulfolipids.

Authors:  Won-Jin Chung; Christopher D Vanderwal
Journal:  Acc Chem Res       Date:  2014-01-08       Impact factor: 22.384

5.  Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Authors:  Matthew L Landry; Dennis X Hu; Grace M McKenna; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2016-04-08       Impact factor: 15.419

6.  Reaction mechanism of organoselenium-catalyzed syn-dichlorination of alkenes: a DFT study.

Authors:  Lijun Fu; Xueli Mu; Baiqing Li
Journal:  J Mol Model       Date:  2018-03-13       Impact factor: 1.810

Review 7.  Catalytic Enantioselective Dihalogenation in Total Synthesis.

Authors:  Matthew L Landry; Noah Z Burns
Journal:  Acc Chem Res       Date:  2018-04-17       Impact factor: 22.384

Review 8.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors:  Scott E Denmark; William E Kuester; Matthew T Burk
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

9.  β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

Authors:  Jakub Saadi; Hisashi Yamamoto
Journal:  Chemistry       Date:  2013-02-19       Impact factor: 5.236

10.  Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.

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