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
收藏
页码：4998 / 5001
页数：4
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