Dynamic Kinetic Spiroketalization/Oxa-Michael Addition Cascade of Alkoxyboronates and Peroxyacetals: Enantio- and Diastereoselective Synthesis of Benzannulated Spiroketals

被引：26

作者：

Midya, Abhisek ^{[1
]}

Maity, Sanjay ^{[1
]}

Ghorai, Prasanta ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Bhopal, Dept Chem, Bhopal By Pass Rd, Bhopal 462066, India

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 47期

关键词：

asymmetric synthesis; benzannulated spiroketals; oxa-Michael addition; organocatalysis; peroxy spiroketals; spiroketals; CATALYTIC ASYMMETRIC TRANSACETALIZATION; AGENT PAPULACANDIN-D; ENANTIOSELECTIVE SYNTHESIS; NATURAL-PRODUCTS; AMINOTHIOUREA CATALYSTS; BIOLOGICAL-ACTIVITY; CARBOXYLIC-ACIDS; FORMAL SYNTHESIS; C-ARYLGLUCOSIDE; BERKELIC ACID;

D O I：

10.1002/chem.201701291

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unified dynamic kinetic spiroketalization/enantioselective oxa-Michael addition cascade of an aromatic ketone tethered to an alkoxyboronate and an enone moiety has been developed using cinchona alkaloid based amino-thiourea/squaramide organocatalysts to provide isobenzofuran-based benzannulated spiroketals with high diastereoselectivities and excellent enantioselectivities. Further, a dynamic kinetic peroxy-hemiacetalization/dynamic kinetic spiroketalization/enantioselective oxa-Michael addition cascade of the above substrates provides the corresponding exo-peroxy-benzannulated spiroketals with outstanding enantio- and diastereoselectivities.

引用

页码：11216 / 11220

页数：5

共 84 条

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