One Pot Synthesis of Optically Active 4-Isoxazolines by Asymmetric Addition of Alkynylzinc Reagents to Nitrones Followed by Cyclization | Zendy

Yutaka Ukaji | Zendy; Katsuhiko Inomata | Zendy; Weilin Wei | Zendy; Masato Kobayashi | Zendy

Open Access

One Pot Synthesis of Optically Active 4-Isoxazolines by Asymmetric Addition of Alkynylzinc Reagents to Nitrones Followed by Cyclization

Author(s) -

Yutaka Ukaji,

Katsuhiko Inomata,

Weilin Wei,

Masato Kobayashi

Publication year - 2009

Publication title -

heterocycles

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.242

H-Index - 64

eISSN - 1881-0942

pISSN - 0385-5414

DOI - 10.3987/com-08-11566

Subject(s) - chemistry , dimethylzinc , optically active , reagent , zinc , formaldehyde , chiral auxiliary , organic chemistry , enantioselective synthesis , combinatorial chemistry , catalysis

One pot synthesis of optically active 4-isoxazolines was achieved by asymmetric addition of alkynylzinc reagents to nitrones utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary followed by cyclization. By addition of dimethylzinc, the cyclization step was accelerated to afford the corresponding 4-isoxazolines with up to 93% ee. Furthermore, a cyclized zinc intermediate could be trapped with formaldehyde to give the corresponding 2,3,4,5-tetrasubstituted 4-isoxazoline with 85% ee. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved

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