Large-Scale Synthesis of Chiral Tetrahydropyran via Asymmetric Allylation Catalyzed by (S)-3,3?-Cl2-BINOL

被引：2

作者：

Li, Ning ^{[1
]}

Li, Guisheng ^{[1
]}

Konrad, Michael ^{[2
]}

Kressierer, Christoph ^{[2
]}

Betzemeier, Bodo ^{[2
]}

Kosnik, Stephanie C. ^{[1
,3
]}

Wu, Lifen ^{[1
,3
]}

Pennino, Scott ^{[1
,3
]}

Lee, Heewon ^{[1
]}

Zhang, Yongda ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Chem Dev, Ridgefield, CT 06877 USA

[2] Boehringer Ingelheim Pharm GmbH & Co KG, Chem Dev, D-88397 Biberach, Germany

[3] Boehringer Ingelheim Pharmaceut Inc, Mat & Analyt Sci, Ridgefield, CT 06877 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2022年 / 26卷 / 10期

关键词：

PDE2; tetrahydropyran; allylation; 3; 3?-Cl2-BINOL; organocatalyst; ENANTIOSELECTIVE SYNTHESIS; EPOXIDE OPENINGS; RECENT PROGRESS; KETONES; INHIBITOR; 6-ENDO; PHOSPHODIESTERASE; METHALLYLATION; ALLYLBORATION; ACTIVATION;

D O I：

10.1021/acs.oprd.2c00258

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Asymmetric synthesis of chiral tetrahydropyran 3, a key intermediate of PDE2 inhibitor 1, has been achieved in five linear steps with a 49% overall yield and >99:1 er on a large scale. The whole chemical process was realized without silica gel chromatography purification, starting from tert-butyl 2-chloro-5-(2-chloroacetyl)benzoate 7. The key features of current synthesis include asymmetric allylation catalyzed by an organocatalyst (S)-3,3 '-Cl2-BINOL under solvent-free conditions.

引用

页码：2973 / 2978

页数：6

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