Literature DB >> 19681592

Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes.

Laura E Bourque1, Pamela A Haile, K A Woerpel.   

Abstract

(-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed.

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Year:  2009        PMID: 19681592      PMCID: PMC2749648          DOI: 10.1021/jo901111j

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


  8 in total

Review 1.  Natural sesquiterpenoids.

Authors:  B M Fraga
Journal:  Nat Prod Rep       Date:  2001-12       Impact factor: 13.423

Review 2.  Marine natural products.

Authors:  D John Faulkner
Journal:  Nat Prod Rep       Date:  2002-02       Impact factor: 13.423

Review 3.  Triterpenoids.

Authors:  J D Connolly; R A Hill
Journal:  Nat Prod Rep       Date:  2001-10       Impact factor: 13.423

Review 4.  Monoterpenoids.

Authors:  D H Grayson
Journal:  Nat Prod Rep       Date:  2000-08       Impact factor: 13.423

5.  Metal-catalyzed rearrangement of homoallylic ethers to silylmethyl allylic silanes in the presence of a Di-tert-butylsilylene source.

Authors:  Pamela A Cleary; K A Woerpel
Journal:  Org Lett       Date:  2005-11-24       Impact factor: 6.005

Review 6.  Diterpenoids.

Authors:  James R Hanson
Journal:  Nat Prod Rep       Date:  2002-04       Impact factor: 13.423

7.  Diastereoselective silacyclopropanations of functionalized chiral alkenes.

Authors:  Tom G Driver; Annaliese K Franz; K A Woerpel
Journal:  J Am Chem Soc       Date:  2002-06-12       Impact factor: 15.419

8.  Mechanism of silver-mediated di-tert-butylsilylene transfer from a silacyclopropane to an alkene.

Authors:  Tom G Driver; K A Woerpel
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419

  8 in total

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