Literature DB >> 10986101

Anti-selective glycolate aldol additions with an oxapyrone boron enolate.

M B Andrus1, B B Sekhar, E L Meredith, N K Dalley.   

Abstract

The boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2-diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers. Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.

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Year:  2000        PMID： 10986101     DOI： 10.1021/ol0002166

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


  7 in total

1.  Silylene transfer to alpha-keto esters and application to the synthesis of gamma-lactones.

Authors:  Brett E Howard; K A Woerpel
Journal:  Tetrahedron       Date:  2009-09-01       Impact factor: 2.457

2.  Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes.

Authors:  Kanicha Sa-ei; John Montgomery
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

3.  Asymmetric Synthesis of the Core of AMPTD, the Key Amino Acid of Microsclerodermins F-I.

Authors:  Cameron M Burnett; Robert M Williams
Journal:  Tetrahedron Lett       Date:  2009-09-30       Impact factor: 2.415

4.  Symbiotic reagent activation: Oppenauer oxidation of magnesium alkoxides by silylglyoxylates triggers second-stage aldolization.

Authors:  Xin Linghu; Andrew D Satterfield; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2006-07-26       Impact factor: 15.419

5.  A sequential o-nitrosoaldol and Grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols.

Authors:  Peng Jiao; Masanori Kawasaki; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis.

Authors:  Inhee Cho; Labros Meimetis; Lee Belding; Michael J Katz; Travis Dudding; Robert Britton
Journal:  Beilstein J Org Chem       Date:  2011-09-22       Impact factor: 2.883

7.  Nickel-Catalyzed Enantioselective Synthesis of Pre-Differentiated Homoallylic syn- or anti-1,2-Diols from Aldehydes and Dienol Ethers.

Authors:  Thomas Q Davies; John J Murphy; Maxime Dousset; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2021-08-19       Impact factor: 15.419
  7 in total

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