title: One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization: highly selective formation of three new bonds and two stereocenters in acyclic systems.
abstract: It's as easy as 1, 2, 3: In a one-pot sequence, two stereocenters and three new bonds were created with high selectivity through an asymmetric alkynylation of acyl silanes, a tandem Brook-type rearrangement and Zn-ene-allene cyclization, the addition of an electrophile, and finally oxidation. The straightforward nature of the synthetic procedure contrasts strongly with the complexity of the densely functionalized products obtained.
authors.affiliation: Schulich Faculty of Chemistry and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 (Israel).
authors.forename: Polina
authors.initials: P
authors.lastname: Smirnov
authors.forename: Jomon
authors.initials: J
authors.lastname: Mathew
authors.forename: Anne
authors.initials: A
authors.lastname: Nijs
authors.forename: Einat
authors.initials: E
authors.lastname: Katan
authors.forename: Miriam
authors.initials: M
authors.lastname: Karni
authors.forename: Carsten
authors.initials: C
authors.lastname: Bolm
authors.forename: Yitzhak
authors.initials: Y
authors.lastname: Apeloig
authors.forename: Ilan
authors.initials: I
authors.lastname: Marek
keywords: Brook rearrangement; acyl silanes; alkynylation; asymmetric synthesis; zinc