Synthesis of Enantiopure 3-Substituted Morpholines

被引：36

作者：

Bornholdt, Jan ^{[1
]}

Felding, Jakob ^{[2
]}

Kristensen, Jesper Langgaard ^{[1
]}

机构：

[1] Univ Copenhagen, Dept Med Chem, DK-2100 Copenhagen, Denmark

[2] LEO Pharma, DK-2750 Ballerup, Denmark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 21期

关键词：

ALPHA-AMINO-ACIDS; CARBON NUCLEOPHILES; REARRANGEMENT; DEPROTECTION; DERIVATIVES; PROTECTION; AZIRIDINES; REAGENTS; ESTERS;

D O I：

10.1021/jo101339g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure 3-substituted morpholines were assembled through ring-opening of a N-2-benzothiazolesulfonyl (Bts) activated aziridine with organocuprates followed by a ring annulation reaction with a vinylsulfonium salt under microwave conditions. Deprotection of the N-Bts group proceeds under very mild conditions with 2-mercaptoacetic acid and LiOH at rt.

引用

页码：7454 / 7457

页数：4

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