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Rh(II)-Catalyzed Enantioselective Cyclopropanation of Olefins with Dimethyl Malonate via in Situ Generated Phenyliodonium Ylide

journal contribution
posted on 2023-05-17, 00:14 authored by Muller, P, Ghanem, A
Olefins are cyclopropanated with dimethyl malonate (1a) iodosylbenzene (PhIO) and a Rh(II) carboxylate catalyst via an in situ generated phenyliodonium ylide (1c). Enantioselectivities of up to 90% for 4-bromostyrene and 98% for pent-1-ene have been observed with (S)-N-4-bromo-1,8-naphthanoyl-tert-leucine (4c) as the chiral ligand. The same catalyst was effective for olefin cyclopropanation with Meldrum's acid, giving cyclopropanes with 96% (with styrene) and 87% ee (with pent-1-ene), respectively.

History

Publication title

Organic Letters

Volume

6

Issue

23

Pagination

4347-4350

ISSN

1523-7060

Department/School

School of Natural Sciences

Publisher

Amer Chemical Soc

Place of publication

1155 16Th St, Nw, Washington, USA, Dc, 20036

Rights statement

Copyright © 2004 American Chemical Society

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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