Literature DB >> 19778012

Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences.

Ming Chen1, Masaki Handa, William R Roush.   

Abstract

The hydroboration of allene 7 with ((d)Ipc)(2)BH at 0 degrees C provides the kinetic allylborane 12Z with >20:1 selectivity. However, when the hydroboration is performed at 85 degrees C, the kinetically formed allylborane isomerizes to give the thermodynamic allylborane 12E with >or=12:1 selectivity. Subsequent treatment of 12Z or 12E with aldehydes at -78 degrees C, followed by oxidative workup, provides the 2-methyl-1,2-diols 8 and 9 in good yield and with 80-92% e.e.

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Year:  2009        PMID： 19778012      PMCID： PMC2762002          DOI： 10.1021/ja904599h

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


  16 in total

1.  Stereoselective synthesis of the C(1)-C(11) fragment of peloruside A.

Authors:  Robert M Owen; William R Roush
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

2.  Dinuclear asymmetric Zn aldol additions: formal asymmetric synthesis of fostriecin.

Authors:  Barry M Trost; Mathias U Frederiksen; Julien P N Papillon; Paul E Harrington; Seunghoon Shin; Brock T Shireman
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

3.  Synthesis of the C(26)-C(42) and C(43)-C(67) pyran-containing fragments of amphidinol 3 via a common pyran intermediate.

Authors:  Jacqueline D Hicks; William R Roush
Journal:  Org Lett       Date:  2008-01-19       Impact factor: 6.005

4.  Formal total synthesis of fostriecin.

Authors:  Yong-Gang Wang; Yuichi Kobayashi
Journal:  Org Lett       Date:  2002-12-26       Impact factor: 6.005

5.  Synthesis of the C(43)-C(67) fragment of amphidinol 3.

Authors:  Jacqueline D Hicks; Eric M Flamme; William R Roush
Journal:  Org Lett       Date:  2005-11-24       Impact factor: 6.005

6.  Total synthesis of fostriecin (CI-920).

Authors:  D L Boger; S Ichikawa; W Zhong
Journal:  J Am Chem Soc       Date:  2001-05-09       Impact factor: 15.419

7.  Total synthesis of (+)-13-deoxytedanolide.

Authors:  Lisa D Julian; Jason S Newcom; William R Roush
Journal:  J Am Chem Soc       Date:  2005-05-04       Impact factor: 15.419

8.  Novel antitumor agents CI-920, PD 113,270 and PD 113,271. II. Isolation and characterization.

Authors:  S S Stampwala; R H Bunge; T R Hurley; N E Willmer; A J Brankiewicz; C E Steinman; T A Smitka; J C French
Journal:  J Antibiot (Tokyo)       Date:  1983-12       Impact factor: 2.649

9.  Letter: Isolation and identification of picronolide, methynolide and neomethynolide produced by Streptomyces venezuelae MCRL-0376.

Authors:  I Maezawa; A Kinumaki; M Suzuki
Journal:  J Antibiot (Tokyo)       Date:  1974-01       Impact factor: 2.649

10.  Formal total synthesis of fostriecin via 1,4-asymmetric induction using cobalt-alkyne complex.

Authors:  Yujiro Hayashi; Hirofumi Yamaguchi; Maya Toyoshima; Kotaro Okado; Takumi Toyo; Mitsuru Shoji
Journal:  Org Lett       Date:  2008-03-04       Impact factor: 6.005
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  21 in total

1.  Diastereo- and enantioselective synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via allenylboronate kinetic resolution with ((d)Ipc)2BH and aldehyde allylboration.

Authors:  Jeng-Liang Han; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-05-30       Impact factor: 6.005

2.  Origins of stereoselectivities in chiral phosphoric acid catalyzed allylborations and propargylations of aldehydes.

Authors:  Hao Wang; Pankaj Jain; Jon C Antilla; K N Houk
Journal:  J Org Chem       Date:  2013-01-18       Impact factor: 4.354

3.  Ni-catalyzed borylative diene-aldehyde coupling: the remarkable effect of P(SiMe3)3.

Authors:  Hee Yeon Cho; James P Morken
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

4.  Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-δ-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

5.  Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-03-16       Impact factor: 6.005

6.  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

7.  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

8.  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

9.  Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane.

Authors:  Jeremy Kister; Amy C DeBaillie; Ricardo Lira; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

10.  Enantioselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols via an enantiodivergent hydroboration-crotylboration reaction of a racemic allenylsilane.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2013-03-27       Impact factor: 6.005
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