Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers.

Journal Article (Journal Article)

We report the catalytic enantio- and diastereoselective preparation of aminocyclopropanes by the cyclopropanation of terminal and (Z )-internal 2-azadienes with donor/acceptor carbenes derived from α-diazoesters. The resulting cyclopropanes bear quaternary carbon stereogenic centers vicinal to the amino-substituted carbon and are formed as a single diastereomer in up to 99:1 er and 97% yield with 0.5 mol % of Rh₂ (DOSP)₄ and only 1.5 equiv of the diazo reagent. Transformations with internal azadienes afford cyclopropanes with three contiguous stereogenic centers.

Full Text

Duke Authors

Malcolmson, Steven

Cited Authors

Shao, X; Malcolmson, SJ

Published Date

September 2019

Published In

Organic Letters

Volume / Issue

21 / 18

Start / End Page

7380 - 7385

PubMed ID

31465235

Pubmed Central ID

PMC6790987

Electronic International Standard Serial Number (EISSN)

1523-7052

International Standard Serial Number (ISSN)

1523-7060

Digital Object Identifier (DOI)

10.1021/acs.orglett.9b02692

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