Literature DB >> 16468764

Reagent-controlled asymmetric homologation of boronic esters by enantioenriched main-group chiral carbenoids.

Paul R Blakemore1, Stephen P Marsden, Huw D Vater.   

Abstract

[reaction: see text] Putative enantioenriched carbenoid species, (R)-1-chloro-2-phenylethylmagnesium chloride (9) and (S)-1-chloro-2-phenylethyllithium (26), generated in situ by sulfoxide ligand exchange from (-)-(R(S),R)-1-chloro-2-phenylethyl p-tolyl sulfoxide (8), effected the stereocontrolled homologation of boronic esters. sec-Alcohols derived from the product boronates by oxidation with basic hydrogen peroxide exhibited % ee closely approaching that of sulfoxide 8 in examples employing Li-carbenoid 26.

Entities:  

Year:  2006        PMID： 16468764     DOI： 10.1021/ol053055k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

Authors:  Liang Zhang; Gabriel J Lovinger; Emma K Edelstein; Adam A Szymaniak; Matteo P Chierchia; James P Morken
Journal:  Science       Date:  2016-01-01       Impact factor: 47.728

2.  Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron "Ate" Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger.

Authors:  Gabriel J Lovinger; Mark D Aparece; James P Morken
Journal:  J Am Chem Soc       Date:  2017-02-16       Impact factor: 15.419

3.  Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Authors:  Hilary A Kerchner; John Montgomery
Journal:  Org Lett       Date:  2016-10-27       Impact factor: 6.005

4.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

5.  Automated iterative Csp3-C bond formation.

Authors:  Daniel J Blair; Sriyankari Chitti; Melanie Trobe; David M Kostyra; Hannah M S Haley; Richard L Hansen; Steve G Ballmer; Toby J Woods; Wesley Wang; Vikram Mubayi; Michael J Schmidt; Robert W Pipal; Greg F Morehouse; Andrea M E Palazzolo Ray; Danielle L Gray; Adrian L Gill; Martin D Burke
Journal:  Nature       Date:  2022-02-08       Impact factor: 49.962

6.  Copper-Catalyzed Carboxylation of Aryl Iodides with Carbon Dioxide.

Authors:  Hung Tran-Vu; Olafs Daugulis
Journal:  ACS Catal       Date:  2013-10-04       Impact factor: 13.084

7.  Assembly-line synthesis of organic molecules with tailored shapes.

Authors:  Matthew Burns; Stéphanie Essafi; Jessica R Bame; Stephanie P Bull; Matthew P Webster; Sébastien Balieu; James W Dale; Craig P Butts; Jeremy N Harvey; Varinder K Aggarwal
Journal:  Nature       Date:  2014-09-11       Impact factor: 49.962

8.  Enantioselective installation of adjacent tertiary benzylic stereocentres using lithiation-borylation-protodeboronation methodology. Application to the synthesis of bifluranol and fluorohexestrol.

Authors:  Stefan Roesner; Daniel J Blair; Varinder K Aggarwal
Journal:  Chem Sci       Date:  2015-04-28       Impact factor: 9.825
  8 in total

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