One-Pot Aminoalkylation of Aldehydes: Diastereoselective Synthesis of Vicinal Diamines with Azaarylmethylamines

Haixing Guan; Xianzhong Cao; Patrick J Walsh; Jianyou Mao

doi:10.1021/acs.orglett.9b03287

One-Pot Aminoalkylation of Aldehydes: Diastereoselective Synthesis of Vicinal Diamines with Azaarylmethylamines

Org Lett. 2019 Nov 1;21(21):8679-8683. doi: 10.1021/acs.orglett.9b03287. Epub 2019 Oct 17.

Authors

Haixing Guan¹, Xianzhong Cao¹, Patrick J Walsh², Jianyou Mao¹

Affiliations

¹ Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering , Nanjing Tech University , 30 South Puzhu Road , Nanjing 211816 , P.R. China.
² Roy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.

PMID: 31622105
DOI: 10.1021/acs.orglett.9b03287

Abstract

A one-pot synthesis of vicinal diamines with azaarylmethylamines and aldehydes is reported. A diverse array of vicinal diamines could be achieved in up to 92% yield with good to excellent diastereoselectivities (up to 20:1). The tandem reaction takes place under mild conditions and provides an alternative strategy for the synthesis of vicinal diamines.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.