New homochiral ketoalcohols from aldol reactions of (+)-isomenthone and reversal of diastereoselectivity

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 9043-9046

  Chughtai, Jameel H ^a   Gardiner, John M ^a   Harris, Steven G ^b   Parsons, Simon ^b   Rankin, David W H ^b   Schwalbe, Carl H ^c  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

^c ASTON UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMENTHONE; KETOL; LITHIUM; LITHIUM DERIVATIVE;

ARTICLE; CHIRALITY; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030780302     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10430-0     Document Type: Article

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20. (a) Kutulya, L. A.;Patsenker, L. D.; Vaschenko, V. V.; Kuznetsov, V. P.; Kulishov, V. I.; Surov, Y. N.; Kravets, V. V. Russ. Chem. Bull. 1995, 44, 1200.
21. (b) Diastereomeric mixtures are typical with menthone.
22. Structures of 2 [R=Me, Ph] and 3 [R=Et] have also been confirmed by X-ray: Chughtai, J. H.; Gardiner, J. M.; Harris, S. G.; Parsons, S.; Rankin, D. W. H.; Schwalbe, C. H. manuscript in preparation, 1997.
23. -1. Compound 2 [R=Et] crystallizes in space group P212121: the absolute configuration is established from the known (unchanged) C2 configuration.
24. HPLC and NMR ratios on crude reaction mixtures: 86-97% yields.
25. Thermal ellipsoids are drawn at 50% probability level. C. K. Johnson, 'ORTEP. Oak Ridge Thermal-Ellipsoid Plot Program' (1976), Oak Ridge National Laboratory, Tennessee, U.S.A.
26. Notably, all the crystal structures (including those to be reported) indicate a ground state preference for trans diaxial configurations of the ring methyl and hydroxyalkyl groups.
27. Gardiner, J. M.; Chughtai, J. H.; Sadler, I. H. manuscript in preparation 1997.