Complementary kinetic and thermodynamic resolution of a chiral biaryl axis

Tetrahedron Letters

Volumn 44, Issue 25, 2003, Pages 4665-4668

  Edwards, David J ^a   Pritchard, Robin G ^a   Wallace, Timothy W ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Axial chirality; Biaryl; Chiral auxiliary; Fused lactam; Kinetic resolution; Valinol

Indexed keywords

2' FORMYLBIPHENYL 2 CARBOXYLIC ACID; 6,7 DIHYDRO 7 ISOPROPYLDIBENZ[C,E]OXALO[3,2 A]AZEPIN 9(4BH) ONE; CARBOXYLIC ACID DERIVATIVE; KETONE DERIVATIVE; LACTAM; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CATALYSIS; CHIRALITY; DIASTEREOISOMER; KINETICS; POLYMERIZATION; TEMPERATURE; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 0038440698     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01091-8     Document Type: Article

References (21)

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14. f (hexane-ethyl acetate, 4:1) 0.28.
15. 2) was 0.0895 (all data). Crystallographic data (excluding structure factors) for compound 6a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 200172. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
16. 2) was 0.0951 (all data). The isopropyl side-chain is disordered over two sites in the ratio 64:36. Figure 2 shows the major of the two rotamers. Crystallographic data (excluding structure factors) for compound 6b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 200173. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
17. The structures 6a-d were generated in Quantum CAChe 4.5 (Fujitsu) and their geometries optimised using semi-empirical methods (CONFLEX and Mechanics applications, augmented MM3 force field). The minimised total steric energies (kcal/mol) were: 6b, 23.4; 6a, 25.2; 6c, 41.4; 6d, 44.1. The main contributor to the difference in total steric energy between 6a and 6c was dihedral strain (+13.6).
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21. For racemisations involving similar considerations, see: (a) Hatsuda, M.; Hiramatsu, H.; Yamada, S.-I.; Shimizu, T.; Seki, M. J. Org. Chem. 2001, 66, 4437-4439; (b) Bringmann, G.; Hinrichs, J.; Henschel, P.; Kraus, J.; Peters, K.; Peters, E.-M. Eur. J. Org. Chem. 2002, 1096-1106.