Asymmetric Transformation of meso-Epoxides by Chiral Lithium Amides.
نویسندگان
چکیده
منابع مشابه
Asymmetric rearrangement of racemic epoxides catalyzed by chiral Brønsted acids.
This paper describes a chiral Brønsted acid catalyzed asymmetric 1,2-rearrangement of racemic epoxides via a hydrogen-shift process for the synthesis of chiral aldehydes, and, followed by a reduction, a variety of optically active alcohols can be furnished in moderate yields with up to 50% ee. Especially, a facile one-pot synthesis of chiral alcohols directly from simple alkenes by a sequential...
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The first asymmetric ring-expansion carbonylation of meso-epoxides to β-lactones is reported. Two structurally diverse chiral Cr(III) chloro complexes in conjunction with Co(2)(CO)(8) were shown to be competent catalytic systems for this transformation, displaying significant levels of asymmetric induction of up to 56% ee.
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Unsymmetrically substituted allenes (1,2-dienes) are inherently chiral and can be prepared in optically pure form. Nonetheless, to date the allene framework has not been incorporated into ligands for asymmetric catalysis. Since allenes project functionality differently than either tetrahedral carbon or chiral biaryls, they may create complementary chiral environments. This study demonstrates th...
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A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aromatic thiol nucleophiles. The resulting β-hydroxyl sulfides are obtained in excellent yield and enantioselectivity.
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Reaction of the chiral crystals of the achiral amides with n-butyllithium in toluene at -80 degrees C gave optically active alcohols in 17-84% ee.
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ژورنال
عنوان ژورنال: Journal of Synthetic Organic Chemistry, Japan
سال: 1996
ISSN: 0037-9980,1883-6526
DOI: 10.5059/yukigoseikyokaishi.54.188