Literature DB >> 17999524

Asymmetric synthesis of 2 degrees- and 3 degrees-Carbinols via B-methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes.

José G Roman1, John A Soderquist.   

Abstract

Simple Grignard procedures provide methallylboranes 1a and 1b in enantiomerically pure form from air-stable precursors in 98% and 95% yields, respectively. These reagents add smoothly to aldehydes and methyl ketones, respectively, providing branched 2 degrees- (6, 69-89%, 94-99% ee) and 3 degrees- (10, 71-87%, 74-96% ee) homoallylic alcohols.

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Year:  2007        PMID： 17999524      PMCID： PMC2563422          DOI： 10.1021/jo701633k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  18 in total

1.  Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones.

Authors:  Scott E Denmark; Jiping Fu
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

Review 2.  Catalytic asymmetric organozinc additions to carbonyl compounds.

Authors:  L Pu; H B Yu
Journal:  Chem Rev       Date:  2001-03       Impact factor: 60.622

3.  Asymmetric allylboration and ring closing alkene metathesis: a novel strategy for the synthesis of glycosphingolipids.

Authors:  A G Barrett; J C Beall; D C Braddock; K Flack; V C Gibson; M M Salter
Journal:  J Org Chem       Date:  2000-10-06       Impact factor: 4.354

4.  A de novo enantioselective total synthesis of (-)-laulimalide.

Authors:  Scott G Nelson; Wing S Cheung; Andrew J Kassick; Mark A Hilfiker
Journal:  J Am Chem Soc       Date:  2002-11-20       Impact factor: 15.419

5.  Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence.

Authors:  Eric M Flamme; William R Roush
Journal:  J Am Chem Soc       Date:  2002-11-20       Impact factor: 15.419

6.  Bidirectional asymmetric allylboration. A convenient asymmetric synthesis of C(2)-symmetric 3-methylenepentane-1,5-diols and rapid access to C(2)-symmetric spiroketals

Authors: 
Journal:  J Org Chem       Date:  2000-01-28       Impact factor: 4.354

7.  Synthesis of the C(21)-C(26) fragment of superstolide A: concerning the stereochemistry of (E)-crotylboration reactions of alaninal derivatives.

Authors:  Neal A Yakelis; William R Roush
Journal:  J Org Chem       Date:  2003-05-16       Impact factor: 4.354

8.  Platinum-catalyzed tandem diboration/asymmetric allylboration: access to nonracemic functionalized 1,3-diols.

Authors:  Jeremy B Morgan; James P Morken
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

9.  3-Boronoacrolein as an exceptional heterodiene in the highly enantio- and diastereoselective Cr(III)-catalyzed three-component [4+2]/allylboration.

Authors:  Xuri Gao; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2003-08-06       Impact factor: 15.419

10.  Asymmetric catalysis of Nozaki-Hiyama allylation and methallylation with a new tridentate bis(oxazolinyl)carbazole ligand.

Authors:  Masahiro Inoue; Takahiro Suzuki; Masahisa Nakada
Journal:  J Am Chem Soc       Date:  2003-02-05       Impact factor: 15.419
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  2 in total

1.  Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability.

Authors:  Abbas Hassan; Ian A Townsend; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2011-08-10       Impact factor: 6.222

2.  Quantum-mechanical study of 10-R-9-borabicyclo[3.3.2]decane alkene hydroboration.

Authors:  Daniel H Ess; Jeremy Kister; Ming Chen; William R Roush
Journal:  J Org Chem       Date:  2009-11-20       Impact factor: 4.354
  2 in total

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