Journal article

Publication year: 2015

Pages: 9996-9999

Journal: Angewandte Chemie International Edition

Volume number: 54

Issue number: 34

Open access status: Bronze

DOI Link: https://doi.org/10.1002/anie.201504756

Publisher: Wiley

Abstract: 

The combined carbometalation/zinc homologation followed by reactions
with α‐heterosubstituted aldehydes and imines proceed through a
chair‐like transition structure with the substituent of the incoming
aldehyde residue preferentially occupying a pseudo‐axial position to
avoid the two gauche interactions. The heteroatom in the axial position
produces a chelated intermediate (and not a Cornforth–Evans transition
structure for α‐chloro aldehydes and imines) leading to a face
differentiation in the allylation reaction. This method provides access
to functionalized products in which three new carbon–carbon bonds and
two to three stereogenic centers, including a quaternary one, were
created in acyclic systems in a single‐pot operation from simple
alkynes.

Harvard Citation style: Vabre, R., Island, B., Diehl, C., Schreiner, P. and Marek, I. (2015) Forming Stereogenic Centers in Acyclic Systems from Alkynes, Angewandte Chemie International Edition, 54(34), pp. 9996-9999. https://doi.org/10.1002/anie.201504756

APA Citation style: Vabre, R., Island, B., Diehl, C., Schreiner, P., & Marek, I. (2015). Forming Stereogenic Centers in Acyclic Systems from Alkynes. Angewandte Chemie International Edition. 54(34), 9996-9999. https://doi.org/10.1002/anie.201504756