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1.
J Org Chem ; 77(18): 8338-43, 2012 Sep 21.
Article in English | MEDLINE | ID: mdl-22900985

ABSTRACT

The direct asymmetric vinylogous Mannich reaction of 3,4-dihalofuran-2(5H)-one with aldimine catalyzed by quinine was first reported, and γ-butenolides have been obtained in excellent yield (up to 98%) and enantioselectivities (up to 95% ee). The synthetic applications of this protocol are demonstrated in the preparations of γ-substituted amino butyrolactones and vicinal amino alcohols.

2.
Chem Commun (Camb) ; 48(42): 5175-7, 2012 May 25.
Article in English | MEDLINE | ID: mdl-22517246

ABSTRACT

A stereoselective [3+2] cycloaddition of isocyanoesters to methyleneindolinones catalyzed by a quinine-based thiourea-tertiary amine has been successfully developed. Just by tuning the protecting groups on substrates, a variety of optically enriched 3,3'-pyrrolidinyl spirooxindole diastereomers could be obtained in excellent enantioselectivities (up to 99% ee).


Subject(s)
Indoles/chemistry , Pyrrolidines/chemistry , Amines/chemistry , Catalysis , Crystallography, X-Ray , Cyclization , Indoles/chemical synthesis , Molecular Conformation , Quinine/chemistry , Stereoisomerism , Thiourea/chemistry
3.
Org Biomol Chem ; 9(13): 4774-7, 2011 Jul 07.
Article in English | MEDLINE | ID: mdl-21614388

ABSTRACT

A series of primary-tertiary diamine catalysts were successfully applied to promote the enantioselective aldol reaction of acetone with ß,γ-unsaturated α-keto esters in excellent yields (up to 99%) and enantioselectivities (up to 96% ee).


Subject(s)
Acetone/chemistry , Diamines/chemistry , Esters/chemistry , Aldehydes/chemistry , Catalysis , Molecular Structure , Stereoisomerism
4.
Chem Commun (Camb) ; 47(19): 5593-5, 2011 May 21.
Article in English | MEDLINE | ID: mdl-21455513

ABSTRACT

An effective double Michael reaction has been disclosed to access spirocyclic oxindoles in high yields (up to 98%) and excellent enantioselectivities (up to 98% ee).

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