Probing the “additive effect” in the proline and proline hydroxamic acid catalyzed asymmetric addition of nitroalkanes to cyclic enones | Zendy

Hanessian Stephen | Zendy; Govindan Subramaniyan | Zendy; Warrier Jayakumar S. | Zendy

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Probing the “additive effect” in the proline and proline hydroxamic acid catalyzed asymmetric addition of nitroalkanes to cyclic enones

Author(s) -

Hanessian Stephen,

Govindan Subramaniyan,

Warrier Jayakumar S.

Publication year - 2005

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.20201

Subject(s) - chemistry , proline , catalysis , hydroxamic acid , amino acid , organic chemistry , stereochemistry , combinatorial chemistry , biochemistry

The effect of chirality and steric bulk of 2,5‐disubstituted piperazines as additives in the conjugate addition of 2‐nitropropane to cyclohexenone, catalyzed by l ‐proline, was investigated. Neither chirality nor steric bulk affects the enantioselectivity of addition, which gives 86–93% ee in the presence of achiral and chiral nonracemic 2,5‐disubstituted piperazines. Proline hydroxamic acid is shown for the first time to be an effective organocatalyst in the same Michael reaction. © 2005 Wiley‐Liss, Inc. Chirality 17:540–543, 2005.

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