Title

Assembly of Tetrahydropyran Derivatives from Aldehydes, Allylboronates, and Syngas by Asymmetric Relay Catalytic Cascade Reaction.

Authors

Li, Lu‐Lu; Su, Yong‐Liang; Han, Zhi‐Yong; Gong, Liu‐Zhu

Abstract

Abstract: An efficient synthesis of highly enantio‐enriched tetrahydropyrans from readily available aldehydes, allylboronates, and syngas has been established by multiply relay catalysis of rhodium and chiral phosphoric acid. The cascade reaction integrates the asymmetric allylboration of aldehydes and alkene hydroformylation, providing a structurally diverse range of products with different workup procedures. The concise synthesis of key chiral building blocks to access herboxidiene and leucascandrolide A demonstrates the high synthetic utility of this method. The cascade reaction employing alkenes to replace aldehydes was also successful.

Subjects

TETRAHYDROPYRANYL compounds; CHEMICAL derivatives; ALDEHYDES; BORONIC esters; SYNTHESIS gas; CHEMICAL reactions

Publication

Chemistry - A European Journal, 2018, Vol 24, Issue 30, p7626

ISSN

0947-6539

Publication type

Academic Journal

DOI

10.1002/chem.201801197