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Org Lett ; 5(12): 2137-40, 2003 Jun 12.
Article in English | MEDLINE | ID: mdl-12790548

ABSTRACT

[reaction: see text] In connection with the known diyne-ene [2 + 2 + 2] cycloaddition reactions mediated by titanium aryloxides, the ability of titanium alkoxides to promote coupling of a titanacyclopentadiene with an alkene has been assessed for the isomerization-free preparation of 1,3-cyclohexadienes. The successful cycloaddition by titanium alkoxides is predicated on the use of homoallylic alcohols as the olefin component. With secondary homoallylic alcohols, high 1,3-diastereoselectivity is observed, which lends itself to enantioselective preparation of functionalized 1,3-cyclohexadienes.


Subject(s)
Alcohols/chemical synthesis , Alkynes/chemistry , Allyl Compounds/chemical synthesis , Titanium/chemistry , Allyl Compounds/chemistry , Cyclization , Cyclopropanes/chemistry , Hydrocarbons, Cyclic/chemical synthesis , Organometallic Compounds/chemistry , Stereoisomerism
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