Literature DB >> 10891257

Diastereoselective alkylations of oxazolidinone glycolates: a useful extension of the Evans asymmetric alkylation.

M T Crimmins1, K A Emmitte, J D Katz.   

Abstract

[reaction: see text] The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of alpha-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols. Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation. Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.

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Year:  2000        PMID： 10891257     DOI： 10.1021/ol006091m

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


  11 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.  A highly convergent approach toward (-)-brevenal.

Authors:  Michael T Crimmins; Mariam Shamszad; Anita E Mattson
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

3.  Enantioselective total synthesis of bistramide A.

Authors:  Michael T Crimmins; Amy C DeBaillie
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

4.  Lithium Amino Alkoxide-Evans Enolate Mixed Aggregates: Aldol Addition with Matched and Mismatched Stereocontrol.

Authors:  Janis Jermaks; Evan H Tallmadge; Ivan Keresztes; David B Collum
Journal:  J Am Chem Soc       Date:  2018-02-19       Impact factor: 15.419

5.  Enantioselective total synthesis of brevetoxin A: unified strategy for the B, E, G, and J subunits.

Authors:  Michael T Crimmins; J Michael Ellis; Kyle A Emmitte; Pamela A Haile; Patrick J McDougall; Jonathan D Parrish; J Lucas Zuccarello
Journal:  Chemistry       Date:  2009-09-14       Impact factor: 5.236

6.  Asymmetric total synthesis of pyranicin.

Authors:  Michael T Crimmins; Danielle L Jacobs
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

7.  Total synthesis of potent antitumor agent (-)-lasonolide A: a cycloaddition-based strategy.

Authors:  Arun K Ghosh; Gangli Gong
Journal:  Chem Asian J       Date:  2008-10-06

8.  Structure Elucidation of Nigricanoside A Through Enantioselective Total Synthesis.

Authors:  Jie Chen; Panduka Koswatta; J Robb DeBergh; Peng Fu; Ende Pan; John B MacMillan; Joseph M Ready
Journal:  Chem Sci       Date:  2015-03-12       Impact factor: 9.825

9.  Total synthesis of annonaceous acetogenins belonging to the non-adjacent bis-THF and non-adjacent THF-THP sub-classes.

Authors:  Ian B Spurr; Richard C D Brown
Journal:  Molecules       Date:  2010-01-21       Impact factor: 4.411

10.  Stereoselective access to tubuphenylalanine and tubuvaline: improved Mn-mediated radical additions and assembly of a tubulysin tetrapeptide analog.

Authors:  Gregory K Friestad; Koushik Banerjee; Jean-Charles Marié; Umesh Mali; Lei Yao
Journal:  J Antibiot (Tokyo)       Date:  2016-02-17       Impact factor: 2.649
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