Literature DB >> 12862446

Rhodium-catalyzed enantioselective diboration of simple alkenes.

Jeremy B Morgan1, Steven P Miller, James P Morken.   

Abstract

Enantioselective catalytic reactions that operate directly on inexpensive unactivated alkenes are extraordinarily useful for the preparation of chiral organic building blocks and new materials. While a number of such processes have been developed, our ability to meet the intensifying demand for inexpensive stereochemically complex materials will require a significant expansion of practical catalytic asymmetric reaction methodology. In this regard, the rhodium-catalyzed enantioselective diboration reaction has been developed in order to address a number of extant problems in catalytic alkene transformation simultaneously. This process provides an enantiomerically enriched reactive dimetalated intermediate which can be converted to a variety of difunctional reaction products.

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Year:  2003        PMID: 12862446     DOI: 10.1021/ja035851w

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


  29 in total

1.  Catalytic Enantioselective Synthesis of anti-Vicinal Silylboronates by Conjunctive Cross-Coupling.

Authors:  Yan Meng; Ziyin Kong; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-19       Impact factor: 15.336

2.  1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis.

Authors:  Daniel Kaiser; Adam Noble; Valerio Fasano; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2019-09-03       Impact factor: 15.419

3.  Atom-Economical Ni-Catalyzed Diborylative Cyclization of Enynes: Preparation of Unsymmetrical Diboronates.

Authors:  Natalia Cabrera-Lobera; M Teresa Quirós; William W Brennessel; Michael L Neidig; Elena Buñuel; Diego J Cárdenas
Journal:  Org Lett       Date:  2019-07-29       Impact factor: 6.005

4.  Enantiomerically enriched tris(boronates): readily accessible conjunctive reagents for asymmetric synthesis.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  J Am Chem Soc       Date:  2014-11-11       Impact factor: 15.419

5.  Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes.

Authors:  Lichao Fang; Lu Yan; Fredrik Haeffner; James P Morken
Journal:  J Am Chem Soc       Date:  2016-02-16       Impact factor: 15.419

6.  Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes.

Authors:  Hee Yeon Cho; James P Morken
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

7.  Vicinal diboronates in high enantiomeric purity through tandem site-selective NHC-Cu-catalyzed boron-copper additions to terminal alkynes.

Authors:  Yunmi Lee; Hwanjong Jang; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-12-30       Impact factor: 15.419

8.  Pt-catalyzed enantioselective diboration of terminal alkenes with B2(pin)2.

Authors:  Laura T Kliman; Scott N Mlynarski; James P Morken
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

9.  Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes.

Authors:  John R Coombs; Fredrik Haeffner; Laura T Kliman; James P Morken
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

Review 10.  Polyborylated reagents for modern organic synthesis.

Authors:  Masaki Shimizu; Tamejiro Hiyama
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2008       Impact factor: 3.493

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