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A Family of Chiral Ferrocenyl Diols: Modular Synthesis, Solid‐State Characterization, and Application in Asymmetric Organocatalysis
Author(s) -
Nottingham Chris,
MüllerBunz Helge,
Guiry Patrick J.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201604840
Subject(s) - organocatalysis , modular design , characterization (materials science) , chemistry , combinatorial chemistry , state (computer science) , organic chemistry , catalysis , computer science , enantioselective synthesis , materials science , nanotechnology , programming language
Readily available chiral diol scaffolds are useful as sources of chirality for asymmetric synthesis, however, few such scaffolds are readily available in enantiopure form. Reported herein is a cheap and modular synthesis of a novel family of chiral ferrocenyl diols in excellent yields with excellent enantio‐ and diastereoselectivity (>99 % ee and 99 % de ). These diols possess not only planar and central chirality, but also axial chirality around the central iron atom. Characterization of these diols by X‐ray crystallography revealed intra‐ and intermolecular hydrogen‐bond networks depending on substitution at the carbinol positions. The potential of these diols as catalysts was subsequently demonstrated in an asymmetric hetero‐Diels–Alder reaction which provided cycloadducts in up to 84 % yield with ee values ranging from −92 to +72 %.