Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines.

Journal Article (Journal Article)

The 1,3-diamine motif appears in numerous complex molecules, yet there are few methods for the stereoselective construction of this moiety. Herein, we demonstrate a stereocontrolled synthesis of 1,3-diamines, which bear up to three contiguous stereogenic centers, through benzylic ring-opening of aziridines with 2-azaallyl anion nucleophiles. Reactions proceed efficiently (yield up to 95%), diastereoselectively (dr up to >20:1), site selectively, and enantiospecifically to deliver products with differentiated amino groups.

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Duke Authors

Malcolmson, Steven

Cited Authors

Li, K; Weber, AE; Tseng, L; Malcolmson, SJ

Published Date

August 2017

Published In

Organic Letters

Volume / Issue

19 / 16

Start / End Page

4239 - 4242

PubMed ID

28771013

Electronic International Standard Serial Number (EISSN)

1523-7052

International Standard Serial Number (ISSN)

1523-7060

Digital Object Identifier (DOI)

10.1021/acs.orglett.7b01886

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