Two-Step One-Pot Synthesis of Benzoannulated Spiroacetals by Suzuki-Miyaura Coupling/Acid-Catalyzed Spiroacetalization

被引：14

作者：

Butkevich, Alexey N. ^{[1
]}

Corbu, Andrei ^{[1
]}

Meerpoel, Lieven ^{[3
]}

Stansfield, Ian ^{[2
]}

Angibaud, Patrick ^{[2
]}

Bonnet, Pascal ^{[3
]}

Cossy, Janine ^{[1
]}

机构：

[1] ESPCI ParisTech, CNRS, Chim Organ Lab, F-75231 Paris 05, France

[2] Janssen Res & Dev, F-27106 Val De Reuil, France

[3] Janssen Res & Dev, B-2340 Beerse, Belgium

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 19期

关键词：

INTRAMOLECULAR ALKYNE HYDROALKOXYLATION; CYCLIC VINYL ETHERS; C-H BORYLATION; NATURAL-PRODUCTS; SPIROKETALS; SPIROCYCLIZATION; BIS(PINACOLATO)DIBORON; RUBROMYCINS; GLYCOSIDES; HYDRIDES;

D O I：

10.1021/ol302088w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted benzoannulated spiroacetals were prepared from (2-haloaryl)alkyl alcohols and dihydropyranyl or dihydrofuranyl pinacol boronates using a Suzuki-Miyaura coupling followed by an acid-catalyzed spirocyclization. Application of the reaction to a glycal boronate provides an approach to annulated spiroacetals in enantiopure form.

引用

页码：4998 / 5001

页数：4

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