Synthesis of Highly Substituted Aminotetrahydropyrans Enabled by Stereospecific Multivector C-H Functionalization

被引：3

作者：

Kang, Guowei ^{[1
]}

Xiao, Li-Jun ^{[1
]}

Hesp, Kevin D. ^{[2
]}

Huh, Chan Woo ^{[3
]}

Lian, Yajing ^{[3
]}

Richardson, Paul ^{[4
]}

Schmitt, Daniel C. ^{[3
]}

Hong, Kai ^{[1
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Treeline Biosci, Watertown, MA 02472 USA

[3] Pfizer Inc, Med Design, Groton, CT 06340 USA

[4] Pfizer Inc, Med Design, San Diego, CA 92121 USA

来源：

ORGANIC LETTERS | 2023年 / 26卷 / 14期

关键词：

TETRAHYDROPYRAN; INHIBITORS; ARYLATION;

D O I：

10.1021/acs.orglett.3c01439

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly substituted aminotetrahydropyrans were synthesizedvia sequentialC-H functionalizations. The process was initiated with a Pd(II)-catalyzedstereoselective gamma-methylene C-H arylation of aminotetrahydropyran,followed by alpha-alkylation or arylation of the corresponding primaryamine. The initial gamma-C-H (hetero)arylation was compatiblewith a range of aryl iodides containing various substituents and providedthe corresponding products in moderate to good yields. The subsequent alpha-alkylation or arylation of the isolated arylated productsproceeded with high diastereoselectivity to afford value-added disubstitutedaminotetrahydropyrans.

引用

页码：2729 / 2732

页数：4

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