Construction of Contiguous Tetrasubstituted Carbon Stereocenters by Intramolecular Crossed Benzoin Reactions Catalyzed by N-Heterocyclic Carbene (NHC) Organocatalyst

Autor: Ryoko Obayashi, Takashi Sakai, Kumiko Akihara, Tadashi Ema
Rok vydání: 2012
Předmět:
Zdroj: Advanced Synthesis & Catalysis. 354:3283-3290
ISSN: 1615-4150
DOI: 10.1002/adsc.201200499
Popis: Bicyclic compounds with two contiguous tetrasubstituted carbon stereocenters at bridgehead positions were synthesized by N-heterocyclic carbene (NHC)-catalyzed intramolecular crossed benzoin reactions of symmetrical compounds. This desymmetrization strategy was applied to asymmetric synthesis with chiral NHC organocatalysts. Transition-state models were proposed to explain the enantioselectivity. A tricyclic compound with three contiguous tetrasubstituted carbon stereocenters was synthesized by a stepwise strategy. The molecular structure and absolute configuration of the (+)-enantiomer of this tricyclic compound were determined by X-ray crystallographic analysis.
Databáze: OpenAIRE