Bulletin of the Korean Chemical Society

2010

DOI: 10.5012/bkcs.2010.31.03.541

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3-Isoxazolidinone: A New Achiral Template for Enantioselective Transformations

Mukund P. Sibi¹,

Brandon Gustafson²,

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Cited by 5 publications

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“…By using 3-isoxazolidinone as a template, the α-methylacrylate reacted smoothly with cyclopentadiene, furnishing the cycloadduct in good yield and with moderate enantioselectivity. 7 Friedel-Crafts Reactions. Zinc triflimide is an excellent catalyst for Friedel-Crafts acylations in ionic liquid.…”

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Zinc Bis(trifluoromethylsulfonyl)imide

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2012

Encyclopedia of Reagents for Organic Synthesis

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“…By using 3-isoxazolidinone as a template, the α-methylacrylate reacted smoothly with cyclopentadiene, furnishing the cycloadduct in good yield and with moderate enantioselectivity. 7 Friedel-Crafts Reactions. Zinc triflimide is an excellent catalyst for Friedel-Crafts acylations in ionic liquid.…”

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confidence: 99%

Zinc Bis(trifluoromethylsulfonyl)imide

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2012

Encyclopedia of Reagents for Organic Synthesis

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ChemInform Abstract: 3‐Isoxazolidinone: A New Achiral Template for Enantioselective Transformations.

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2010

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A New Achiral Template for Enantioselective Transformations. -The Diels-Alders reaction of 3-isoxazolidinone acrylate (Ia) with cyclopentadiene in the presence of a chiral bisoxazoline proceeds with high diastereo-and enantioselectivity. The analogous reaction of crotonate (Ib) is less efficient with respect to selectivity. -(SIBI*, M. P.; GUSTAFSON, B.; COULOMB, J.; Bull. Korean Chem.

Evaluation of Achiral Templates with Fluxional Brønsted Basic Substituents in Enantioselective Conjugate Additions

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2014

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Enantioselective conjugate addition of malononitrile to pyrazolidinone-derived enoates proceeds in excellent yields and high enantioselectivities. A comparison of fluxional substituents with and without a Brønsted basic site and their impact on selectivity is detailed. Molecular sieves as an additive were found to be essential to achieve high enantioselectivity.

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