Intramolecular transfer of axial to central chirality in the Strecker reaction. Synthesis and stereochemistry of 5,7-dicyano-6,7-dihydro-5H- dibenz[c,e]azepines

Tetrahedron

Volumn 55, Issue 25, 1999, Pages 7893-7906

  Tichý, Miloš ^a   Buděšínský, Miloš ^a   Günterová, Jana ^a   Závada, Jiří ^a   Podlaha, Jaroslav ^b   Císařová, Ivana ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Asymmetric induction; Biaryls; NMR; X ray crystal structures

Indexed keywords

5,7 DICYANO 6,7 DIHYDRO 5H DIBENZ[C,E]AZEPINE DERIVATIVE; ALDEHYDE; AMINO ACID DERIVATIVE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0033580812     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00399-3     Document Type: Article

References (12)

1. Th Ed., P. 965, Wiley 1992, and references cited therein.
2. (a) Takahashi K., Mikajiri T., Kurita H., Ogura K., Iida H.: J. Org. Chem. 1985, 50, 4372-4375;
3. (b) Bonin M., Chiaroni A., Riche C., Beloeul J.-C., Grierson D.S., Husson H.-P.: J. Org. Chem. 1987, 52, 382-385;
4. (c) Takahashi K., Saitoh H., Ogura K., Iida H.: Heterocycles 1986, 24, 2905-2910.
5. This is the tenth of the series of papers dealing with axially chiral biaryl amino acids, their derivatives and analogues; for previous papers see ref. 4.
6. (a) Tichý M., Holanová J., Závada J.: Tetrahedron: Asymmetry 1998, 9, 3497-3504;
7. (b) Ridvan L., Buděšínský M., Tichý M., Závada J.: Tetrahedron, Submitted.
8. Only a few examples of an intramolecular transfer of axial into central chirality have been so far recorded in the literature, our pertinent observation concerning the Stevens rearrangement of the axially twisted dihydroazepinium and dihydrothiepinium salts being probably the most recent example (see reference 6).
9. Stará I.G., Starý I., Tichý M., Závada J., Hanuǎ V.: J. Amer. Chem. Soc. 1994, 116, 5084-5088.
10. Müllen K., Heinz W., Klärner F.-G., Roth W.R., Kindermann I., Adamczak O., Wette M., Lex J.: Chem. Ber. 1990, 123, 2349-2371.
11. Sheldrick, G.M. Shelxl-93. Program for Crystal Structure Refinement from Diffraction Data, University of Göttingen, 1993.
12. Sheldrick, G.M. Acta Crystallogr. 1990, A46, 467-473.