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Enolate Additions to a Chiral 3-Hydroxypropionate 2,3-Dication Equivalent. Enantioselective Synthesis of β,δ-Dihydroxy Esters
journal contribution
posted on 1997-05-16, 00:00 authored by W. Zhen, K.-H. Chu, M. RosenblumThe use of optically active dicarbonyl
cyclopentadienyliron(vinyl ether) BF4 salts,
3 and 4, as
enantioselective 3-hydroxypropionate 2,3-dication equivalents is
outlined. Complexes 3 and 4 are
readily available by exchange etherification of 2, and these
have been transformed to enantiomeric
dicarbonyl
(η-cyclopentadienyliron)(η2-1-methoxypropene)
BF4 5 and ent-5. Complex
5 has been
converted to the corresponding p-methoxybenzyloxy vinyl
ether complex 7 by exchange etherification.
Condensation of this salt with a number of terminal and nonterminal
enolates yields adducts, which
are then transformed by redox-promoted alkoxycarbonylation, followed by
alcohol deprotection, to
optically active 2-methyl-3-hydroxy-5 keto esters. 1,3-Reduction of
these ketols can be effected to
give either syn- or anti-1,3-diols and thence
their related pentanolides.
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diolEnantioselectivemethoxybenzyloxy vinyl etherHydroxypropionateestersComplexexchange etherificationEstermethoxypropeneketolBF 4 5DihydroxyEquivalenthydroxypropionatepentanolidedicarbonyldeprotectionenantiomericentsynSynthesiCondensationChiralequivalentnonterminal enolates yields adductsenantioselectiveComplexeDicationcyclopentadienylironketomethyldicationBF 4 saltsalkoxycarbonylationEnolate
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