Enantiomerization dynamics and a catalytic dynamic resolution of N-trimethylallyl-2-lithiopyrrolidine.
The barriers to enantiomerization of N-trimethylallyl-2-lithiopyrrolidine have been measured in the presence of sparteine,1, N,N'-diisopropylbispidine, 2, and diaminoalkoxide 3. We have additionally demonstrated a rare example of a catalytic dynamic resolution using either of two ligands, achieving enantiomer ratios of up to 93:7.
Beng
Timothy K
TK
Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA.
Yousaf
Taher I
TI
Coldham
Iain
I
Gawley
Robert E
RE
D000498:Allyl Compounds / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D002384:Catalysis; D003959:Diamines / Q000737:chemistry; D007700:Kinetics; D008024:Ligands; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013034:Sparteine / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
D000498:Allyl Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003959:Diamines; D008024:Ligands; D009942:Organometallic Compounds; D011759:Pyrrolidines; C495809:bispidine; C450681:phenyllithium; D013034:Sparteine; D008094:Lithium