Synthesis of enantiopure 3-substituted morpholines

Jan Bornholdt; Jakob Felding; Jesper Langgaard Kristensen

doi:10.1021/jo101339g

Synthesis of enantiopure 3-substituted morpholines

Jan Bornholdt, Jakob Felding, Jesper Langgaard Kristensen

31 Citations (Scopus)

Abstract

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.

Original language	English
Journal	Journal of Organic Chemistry
Volume	75
Issue number	21
Pages (from-to)	7454-7457
ISSN	0022-3263
DOIs	https://doi.org/10.1021/jo101339g
Publication status	Published - 5 Nov 2010

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Former Faculty of Pharmaceutical Sciences

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title = "Synthesis of enantiopure 3-substituted morpholines",

abstract = "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.",

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AU - Bornholdt, Jan

AU - Felding, Jakob

AU - Kristensen, Jesper Langgaard

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N2 - 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.

AB - 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.

KW - Former Faculty of Pharmaceutical Sciences

U2 - 10.1021/jo101339g

DO - 10.1021/jo101339g

M3 - Journal article

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SP - 7454

EP - 7457

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Synthesis of enantiopure 3-substituted morpholines

Abstract

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