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Assembly of Tetrahydropyran Derivatives from Aldehydes, Allylboronates, and Syngas by Asymmetric Relay Catalytic Cascade Reaction
Author(s) -
Li LuLu,
Su YongLiang,
Han ZhiYong,
Gong LiuZhu
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801197
Subject(s) - hydroformylation , tetrahydropyran , syngas , cascade , chemistry , cascade reaction , combinatorial chemistry , catalysis , aldehyde , alkene , rhodium , organic chemistry , ring (chemistry) , chromatography
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.