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Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes
Author(s) -
Kennington Stuart C. D.,
Teloxa Saul F.,
MelladoHidalgo Miguel,
Galeote Oriol,
Puddu Sabrina,
Bellido Marina,
Romea Pedro,
Urpí Fèlix,
Aullón Gabriel,
FontBardia Mercè
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202104352
Subject(s) - aldol reaction , enantioselective synthesis , chemistry , catalysis , adduct , nickel , combinatorial chemistry , stereochemistry , organic chemistry
A direct and asymmetric aldol reaction of N ‐acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The reaction gives the corresponding O ‐TIPS‐protected anti ‐aldol adducts in high yields and with remarkable stereocontrol and atom economy. Furthermore, the straightforward removal of the achiral scaffold provides enantiomerically pure intermediates of synthetic interest, which involve precursors for anti ‐α‐amino‐β‐hydroxy and α,β‐dihydroxy carboxylic derivatives. Theoretical calculations explain the observed high stereocontrol.