Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α-Carbonyl Sulfoxonium Ylides

被引：17

作者：

Vidal, Lucas ^{[1
]}

Chen, Pan -Pan ^{[2
]}

Nicolas, Eva ^{[1
]}

Hackett, Andrew ^{[1
,3
]}

Robertson, Craig M. ^{[1
]}

Houk, Kendall N. ^{[2
]}

Aissa, Christophe ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, England

[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[3] Univ Manchester, Fac Biol Med & Hlth, Manchester Acad Hlth Sci Ctr, Sch Biol Sci, Manchester M13 9PT, England

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 46期

基金：

美国国家科学基金会;

关键词：

CARBENE PRECURSORS; CRYSTAL-STRUCTURES; DIAZOACETATES; COMPLEXES; BOND; INSERTION;

D O I：

10.1021/acs.orglett.2c03396

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective cyclopropanation of alpha-carbonyl sulfoxo-nium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular cyclopropanation of SY in the presence of a chiral diene in up to 96% yield and 98% enantioselectivity. Moreover, density functional theory calculations suggest that the re face of the olefin preferably attacks an iridium carbene intermediate in an asynchronous concerted step that is independent of the geometry of the olefin. 00 / 0 I1 X'jf Ir(I) cat./L" 1,2-DCE, r.t. H R2 R3 R3 X = 0, NR, CH2; n = 1, 2; R1 -R3 = H (hetero)aryl, alkenyl, alkyl L" Ph Ph from DFT studies

引用

页码：8503 / 8508

页数：6

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