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Asymmetric Synthesis of Fluorinated Monoterpenic Alkaloid Derivatives from Chiral Fluoroalkyl Aldimines via the Pauson‐Khand Reaction
Author(s) -
Llobat Alberto,
Sedgwick Daniel M.,
Cabré Albert,
Román Raquel,
Mateu Natalia,
Escorihuela Jorge,
MedioSimón Mercedes,
Soloshonok Vadim,
Han Jianlin,
Riera Antoni,
Fustero Santos
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901504
Subject(s) - chemistry , aldimine , pauson–khand reaction , enyne , organic chemistry , alkaloid , combinatorial chemistry , catalysis
Abstract Enantioenriched fluorinated monoterpenic alkaloid analogues were synthesised, employing a strategy based on the previously undescribed diastereoselective propargylation of fluorinated tert ‐butanesulfinyl imines, and subsequent Pauson‐Khand reaction of resulting enyne derivatives, carried out both stoichiometrically and catalytically. The Pauson‐Khand reaction tolerated both substituted alkenes and alkynes, and took place in good yields and diastereoselectivities, even when applied to a gram‐scale synthesis.