Literature DB >> 17850161

Diastereoselective Prins-type reaction of cycloalkenylcyclopropanol silyl ethers and alpha,beta-unsaturated aldehyde acetals.

Ivan L Lysenko1, Heong-Sub Oh, Jin Kun Cha.   

Abstract

Electrophilic addition of 1-(1-cyclohexenyl)-1-cyclopropanol trimethylsilyl ether to alpha,beta-unsaturated aldehyde acetals under Lewis acidic conditions proceeds with good to excellent diastereoselectivity to afford spirocyclobutanones containing three contiguous stereocenters. A convenient entry to enantioselective syntheses is available by use of a nonracemic C2-symmetric acetal. Elaboration of the resulting adducts provides ready access to medium-sized carbocycles.

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Year:  2007        PMID： 17850161      PMCID： PMC2597285          DOI： 10.1021/jo071272o

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


  15 in total

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Authors:  J H Youn; J Lee; J K Cha
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9.  Radical fragmentation of omega-bromoalkyl cyclobutanones. A modular approach to eight-membered carbocycles.

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10.  Stereoselective synthesis of 2,4,6-trisubstituted tetrahydropyrans by the use of cyclopropanols as homoenols.

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Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336
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  2 in total

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