Axially chiral benzamides: Diastereoselective nucleophilic additions to planar chiral (N,N-diethyl-2-acyl-6-methylbenzamide)chromium complexes

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3443-3446

  Koide, Hiroshige ^a   Uemura, Motokazu ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Atropisomerism; Benzenes; Chromium and compounds; Complexes

Indexed keywords

CHROMIUM DERIVATIVE; N,N DIETHYL 2 ACYL 6 METHYLBENZAMIDE CHROMIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CHROMATOGRAPHY; COMPLEX FORMATION; METAL BINDING; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033597322     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00462-1     Document Type: Article

References (25)

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14. 4 Axial N,N-dihexyl-2-alkyl-1-naphthamides were obtained with modest optical purity in a low yield by deprotonation under a combination of s-butyllithium and (-)-sparteine: Thayumanavan, S.; Beak, P.; Curran, D. P. Tetrahedron Lett. 1996, 37, 2899-2902.
15. 5 Clayden, J.; Pink, J. H. Angew. Chem. Int. Ed. Engl. 1998, 37, 1937-1939.
16. 6 Koide, H.; Uemura, M. Chem. Commun. 1998, 2483-2484.
17. ax shows the axial chirality.
18. 8 The organocerium reagents were prepared by the following literature method: Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233-4236.
19. 9 Some reviews; Solladié-Cavallo, A.; Advances in Metal-Organic Chemistry, Ed. by L. S. Liebeskind, JAI Press, Greenwich, 1989, vol. 1. p. 99; Davies, S. G.; McCarthy, T. D. Comprehensive Organometallic Chemistry II,Eds. by Abel, E. W.; Stone, F. G.; Wilkinson, G. Elsevier, 1995, vol. 12, p. 1039.
20. 9 Some reviews; Solladié-Cavallo, A.; Advances in Metal-Organic Chemistry, Ed. by L. S. Liebeskind, JAI Press,Greenwich, 1989, vol. 1. p. 99; Davies, S. G.; McCarthy, T. D. Comprehensive Organometallic Chemistry II, Eds. by Abel, E. W.; Stone, F. G.; Wilkinson, G. Elsevier, 1995, vol. 12, p. 1039.
21. 10 The carbonyl oxygen is oriented upper side to the chromium-complexd arene with 4° incline, and the angle between N-C=O plane and the ring is 91°.
22. 11 In the reactions of tricarbonylchromium-complexed benzaldehydes a possessing bulky ortho triisopropylsilyl substituent with alkyl lithium and Grignard reagents, the diastereomers were selectively obtained via two conformers depending on the nature of nucleophile: Davies, S. G.; Goodfellow, C. L. Synlett, 1989, 59-62.
23. 3) of the other enantiomerically pure axial benzamides 8, 9, 10 and 11 are as follows: 8 (R = Et) +67.5 (c 0.27); 9 (R = Et) -14.0 (c 0.20); 10 (R = Me) -69.0 (c 0.30); 10 (R = Et) -67.2 (c 0.27); 11 (R = Me) +12.0 (c 0.10); 11 (R = Et) +14.0 (c 0.20).
24. 13 Enantiomeric excess was determined by HPLC with Chiralpack OD-H.
25. 2.