Fine-tunable organocatalysts bearing multiple hydrogen-bonding donors for construction of adjacent quaternary and tertiary stereocenters via a michael reaction

Chemistry - A European Journal

Volumn 14, Issue 29, 2008, Pages 8780-8783

  Zhang, Zhi Hai ^a   Dong, Xiu Qin ^a   Chen, Dong ^a   Wang, Chun Jiang ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Hydrogen bonds; Michael addition; Organocatalysis

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; ESTERS; HYDROGEN; NONMETALS; REACTION KINETICS; THEOREM PROVING;

ASYMMETRIC CATALYSIS; BIFUNCTIONAL; CARBON NUCLEOPHILES; CONTROL EXPERIMENTS; DIASTEREOSELECTIVITY; KETOESTERS; MICHAEL ADDITION; MICHAEL ADDITIONS; MICHAEL REACTIONS; NITROOLEFINS; OPTIMAL EXPERIMENTAL CONDITIONS; OPTIMIZED REACTION CONDITIONS; ORGANOCATALYSIS; ORGANOCATALYSTS; TERTIARY STEREOCENTERS;

HYDROGEN BONDS;

EID: 55049089084     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801420     Document Type: Article

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63. 3 (92% yield, dr 75:25, ee 73%); EtOAc (88% yield, dr 74:26, ee 87%); MeCN (91 % yield, dr 87:13, ee 73%); DMSO (70% yield, dr 64:36, ee 6%); MeOH (87% yield, dr 85:15, ee 0%).
64. The absoluted configurations of the major products were assigned by HPLC and optical rotation comparisons with the published results (see Supporting Information for details).