Literature DB >> 12182605

The first example of enantioselective allyl transfer from a linear homoallylic alcohol to an aldehyde.

Teck-Peng Loh1, Chi-Lik Ken Lee, Kui-Thong Tan.   

Abstract

[reaction: see text] The first example of enantioselective linear homoallylic alcohol transfer reaction was revealed. In all cases, the whole rearrangement is thermodynamically favorable and a steric effect is the driving force of this reaction. The preservation of the stereocenter and olefin geometry together with the isolation of gamma-adduct homoallylic alcohols in one isomeric form have warranted the proposed mechanism.

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Year:  2002        PMID: 12182605     DOI: 10.1021/ol0263999

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


  5 in total

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3.  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
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Review 4.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
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5.  Solvolysis of a tetrahydropyranyl mesylate: mechanistic implications for the Prins cyclization, 2-oxonia-cope rearrangement, and Grob fragmentation.

Authors:  Ramesh Jasti; Scott D Rychnovsky
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

  5 in total

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