Work

The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA

Year: 2009

Type: article

Abstract: The kinetics of enantiomerization and dynamic thermodynamic resolution (DTR) of N-Boc-2-lithiopiperidine have been measured, revealing significant differences in enthalpy and entropy for these processes and a role for the achiral ligand TMEDA; the racemization and the DTR are catalytic and first order in [TMEDA], and this has implications for asymmetric synthesis with chiral organolithiums.

Source: Chemical Communications

DOI: 10.1039/b911024k

Authors: Iain Coldham, Daniele Leonori, Timothy K. Beng, Robert E. Gawley

Institutions: University of Sheffield, University of Arkansas at Fayetteville

Language: English

Topic: Coordination Chemistry and Organometallics

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: U.S. Public Health Service, Engineering and Physical Sciences Research Council, National Center for Research Resources

Awards: Center for Protein Structure and Function, Determining the Barrier to Inversion of Chiral Organometallics, G7772536260, G8085124965