Rh(II)-catalyzed enantioselective cyclopropanation of olefins with dimethyl malonate via in situ generated phenyliodonium ylide

被引：65

作者：

Muller, P ^{[1
]}

Ghanem, A ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 23期

关键词：

D O I：

10.1021/ol048159u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Olefins are cyclopropanated with dimethyl malonate (1a) iodosylbenzene (Ph1 = O) and a Rh(II) carboxylate catalyst via an in situ generated phenyliodonium ylide (1c). Enantioselectivilies 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.

引用

页码：4347 / 4350

页数：4

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