Double Chiral Induction Enables a Stereoselective Carbonyl Allylation with Simple Alkenes under the Sequential Catalysis of Palladium Complex and Chiral Phosphoric Acid.

Autor: Li LL; Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China , Hefei 230026, China., Tao ZL; Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China , Hefei 230026, China., Han ZY; Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China , Hefei 230026, China., Gong LZ; Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China , Hefei 230026, China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2017 Jan 06; Vol. 19 (1), pp. 102-105. Date of Electronic Publication: 2016 Dec 20.
DOI: 10.1021/acs.orglett.6b03378
Abstrakt: An enantioselective carbonyl allylation of aldehydes with simple alkenes has been achieved via a one-pot protocol consisting of a Pd-catalyzed allylic C-H borylation with bis(pinanediolato)diboron and a chiral Brønsted acid catalyzed asymmetric allylborylation, delivering homoallylic alcohols in high yields and with excellent diastereo- and enantioselectivities. The double chiral induction of chiral allylic borate and chiral phosphoric acid allows the reaction to give excellent stereoselectivities.
Databáze: MEDLINE