Literature DB >> 16390128

Sequential Pd-catalyzed asymmetric allene diboration/alpha-aminoallylation.

Joshua D Sieber1, James P Morken.   

Abstract

Pd-catalyzed enantioselective diboration of prochiral allenes provides adducts which participate in highly selective allylation reactions with primary imines. The allylation product is a vinyl boronate which may be oxidized to give nonracemic Mannich products (87-97% ee). Alternatively, enantiomerically enriched homoallylic amine derivatives may be obtained by protonation and Suzuki cross-coupling of the vinyl boronate.

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Year:  2006        PMID： 16390128     DOI： 10.1021/ja057020r

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


  21 in total

1.  Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

2.  Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Authors:  Robert E Kyne; Michael C Ryan; Laura T Kliman; James P Morken
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

3.  Control of chemoselectivity in asymmetric tandem reactions: Direct synthesis of chiral amines bearing nonadjacent stereocenters.

Authors:  Zhe Li; Bin Hu; Yongwei Wu; Chao Fei; Li Deng
Journal:  Proc Natl Acad Sci U S A       Date:  2018-02-05       Impact factor: 11.205

4.  Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.

Authors:  Jeremy Kister; Philippe Nuhant; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Org Lett       Date:  2011-03-04       Impact factor: 6.005

5.  Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.

Authors:  Philippe Nuhant; Jeremy Kister; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

6.  Regioselective allene hydrosilylation catalyzed by N-heterocyclic carbene complexes of nickel and palladium.

Authors:  Zachary D Miller; Wei Li; Tomás R Belderrain; John Montgomery
Journal:  J Am Chem Soc       Date:  2013-10-03       Impact factor: 15.419

7.  Orthogonal reactivity in boryl-substituted organotrifluoroborates.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

8.  Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin-Hammett controlled double asymmetric crotylboration reactions of (S)-E-αphenyldimethylsilyl( d diisopinocampheyl)-crotylborane.

Authors:  Ming Chen; William R Roush
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

9.  Enantiodivergent Hydroboration Reactions of a Racemic Allenylsilane with Diisopinocampheylborane and Curtin-Hammett Controlled Double Asymmetric Crotylboration Reactions of (S)-E-α-phenyldimethylsilyl( d diisopinocampheyl)-crotylborane.

Authors:  Ming Chen; William R Roush
Journal:  Tetrahedron       Date:  2013-07-01       Impact factor: 2.457

10.  Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419
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