Literature DB >> 22694052

Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols.

Zhanjie Li1, Brendan T Parr, Huw M L Davies.   

Abstract

The tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor rhodium carbenoids and chiral allyl alcohols is a convergent C-C bond forming process, which generates two vicinal stereogenic centers. Any of the four possible stereoisomers can be selectively synthesized by appropriate combination of the chiral catalyst Rh(2)(DOSP)(4) and the chiral alcohol.

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Year:  2012        PMID： 22694052      PMCID： PMC3413634          DOI： 10.1021/ja303023n

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


  31 in total

1.  Intramolecular generation and [2,3]-sigmatropic rearrangement of oxonium ylides.

Authors:  M C Pirrung; J A Werner
Journal:  J Am Chem Soc       Date:  1986-09-01       Impact factor: 15.419

2.  Enantioselective copper-catalyzed intramolecular O-H insertion: an efficient approach to chiral 2-carboxy cyclic ethers.

Authors:  Shou-Fei Zhu; Xiao-Guang Song; Yu Li; Yan Cai; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2010-10-29       Impact factor: 15.419

3.  Catalytic enantioselective O-H insertion reactions.

Authors:  Thomas C Maier; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2006-04-12       Impact factor: 15.419

4.  Total synthesis of lehualide B by allylic alcohol-alkyne reductive cross-coupling.

Authors:  Valer Jeso; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

5.  Iterative approach to polycyclic ethers based on stereoselective oxonium ylide [2,3]-shifts.

Authors:  F P Marmsäter; F G West
Journal:  J Am Chem Soc       Date:  2001-05-30       Impact factor: 15.419

6.  Rapid access to α-alkoxy and α-amino acid derivatives through safe continuous-flow generation of diazoesters.

Authors:  Hannah E Bartrum; David C Blakemore; Christopher J Moody; Christopher J Hayes
Journal:  Chemistry       Date:  2011-07-27       Impact factor: 5.236

7.  Diazo reagents with small steric footprints for simultaneous arming/SAR studies of alcohol-containing natural products via O-H insertion.

Authors:  Supakarn Chamni; Qing-Li He; Yongjun Dang; Shridhar Bhat; Jun O Liu; Daniel Romo
Journal:  ACS Chem Biol       Date:  2011-09-28       Impact factor: 5.100

8.  Parallel kinetic resolution approach to the cyathane and cyanthiwigin diterpenes using a cyclopropanation/Cope rearrangement.

Authors:  Laura C Miller; J Maina Ndungu; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Catalyst and ring size effects on periselectivity of oxonium ylide rearrangements.

Authors:  Fredrik P Marmsäter; John A Vanecko; F G West
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

10.  Highly enantioselective insertion of carbenoids into O-H bonds of phenols: an efficient approach to chiral alpha-aryloxycarboxylic esters.

Authors:  Chao Chen; Shou-Fei Zhu; Bin Liu; Li-Xin Wang; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2007-09-29       Impact factor: 15.419
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  12 in total

1.  A Stereoselective [3+1] Ring Expansion for the Synthesis of Highly Substituted Methylene Azetidines.

Authors:  Steven C Schmid; Ilia A Guzei; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-01       Impact factor: 15.336

2.  Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides.

Authors:  Zhikun Zhang; Zhe Sheng; Weizhi Yu; Guojiao Wu; Rui Zhang; Wen-Dao Chu; Yan Zhang; Jianbo Wang
Journal:  Nat Chem       Date:  2017-06-05       Impact factor: 24.427

3.  Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides.

Authors:  Bin Xu; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-17       Impact factor: 15.336

4.  Scope and mechanistic analysis of the enantioselective synthesis of allenes by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and propargylic alcohols.

Authors:  Zhanjie Li; Vyacheslav Boyarskikh; Jørn H Hansen; Jochen Autschbach; Djamaladdin G Musaev; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2012-09-11       Impact factor: 15.419

5.  Reaction Mechanism of Li and Mg Carbenoid Cyclopropanations: Metal-π and σ Interactions.

Authors:  Daniel Villablanca; Rocio Durán; Al Mokhtar Lamsabhi; Barbara Herrera
Journal:  ACS Omega       Date:  2019-11-08

6.  Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides.

Authors:  Vaishnavi N Nair; Volga Kojasoy; Croix J Laconsay; Wang Yeuk Kong; Dean J Tantillo; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2021-06-14       Impact factor: 16.383

7.  Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study.

Authors:  Graeme Barker; David G Johnson; Paul C Young; Stuart A Macgregor; Ai-Lan Lee
Journal:  Chemistry       Date:  2015-08-06       Impact factor: 5.236

8.  Gold(I)-catalysed direct thioetherifications using allylic alcohols: an experimental and computational study.

Authors:  Lorena Herkert; Samantha L J Green; Graeme Barker; David G Johnson; Paul C Young; Stuart A Macgregor; Ai-Lan Lee
Journal:  Chemistry       Date:  2014-07-30       Impact factor: 5.236

9.  Highly stereoselective synthesis of cyclopentanes bearing four stereocentres by a rhodium carbene-initiated domino sequence.

Authors:  Brendan T Parr; Huw M L Davies
Journal:  Nat Commun       Date:  2014-08-01       Impact factor: 14.919

10.  Synthesis of a Hominal Bis(difluoromethyl) Fragment.

Authors:  Viktor Ivasyshyn; Hans Smit; Ryan C Chiechi
Journal:  ACS Omega       Date:  2019-08-19
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