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Quaternary Stereogenic Carbon Atoms in Complex Molecules by an Asymmetric, Organocatalytic, Triple‐Cascade Reaction
Author(s) -
Pe Oriol,
Carlone Armando,
Mazzanti Andrea,
Locatelli Manuela,
Sambri Letizia,
Bartoli Giuseppe,
Melchiorre Paolo
Publication year - 2008
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.200800440
Subject(s) - stereocenter , cascade , carbon fibers , cascade reaction , chemistry , cyclohexene , quaternary carbon , stereochemistry , combinatorial chemistry , enantioselective synthesis , computer science , catalysis , organic chemistry , algorithm , chromatography , composite number
Triple (super) attack : The use of 2‐cyanoacrylate derivatives 2 —the main component of one of the most used superglue solutions—in an asymmetric, organocatalytic, triple‐cascade reaction allows the direct synthesis of tri‐ and tetrasubstituted cyclohexene carbaldehydes 4 with three or four stereogenic carbon atoms, one of which is quaternary by all‐carbon substitution, with complete enantioselectivity (>99 % ee ; see scheme).