Asymmetric Synthesis of Chiral Aza-macrodiolides via Iridium-Catalyzed Cascade Allylation/Macrolactonization

被引：17

作者：

Xiong, Qi ^{[1
]}

Xiao, Lu ^{[1
]}

Dong, Xiu-Qin ^{[1
,2
]}

Wang, Chun-Jiang ^{[1
,3
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Engn Res Ctr Organosilicon Cpds & Mat, Minist Educ, Wuhan 430072, Peoples R China

[2] Wuhan Univ, Suzhou Inst, Suzhou 215123, Jiangsu, Peoples R China

[3] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 230021, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 13期

基金：

中国国家自然科学基金;

关键词：

RING-CLOSING METATHESIS; N-HETEROCYCLIC CARBENE; VINYLETHYLENE CARBONATES; DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; MACROCYCLIZATION; CONSTRUCTION; MACROLIDES; MACROLACTONIZATION; REARRANGEMENT;

D O I：

10.1021/acs.orglett.2c00942

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iridium-catalyzed cascade allylation/macrolactonization between vinylethylene carbonate (VEC) and isatoic anhydride derivatives was successfully developed, readily generating a wide range of C-2-symmetric chiral macrodiolides bearing 14-membered rings in moderate to good yields with excellent diastereoselectivities and enantioselectivities (generally 99% ee). Control experiments revealed that racemic VEC as the precursor of electrophilic iridium-pi-allyl species underwent kinetic resolution process. This expedient protocol features easily available substrates, excellent stereoselective control, and high step economy.

引用

收藏

页码：2579 / 2584

页数：6

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