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Volumn 67, Issue 21, 2002, Pages 7319-7328

Novel stereocontrolled addition of allylmetal reagents to α-imino esters: Efficient synthesis of chiral tetrahydroquinoline derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATION REACTION; STEREODIFFERENTIATION REACTIONS;

EID: 0037131374     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020327d     Document Type: Article
Times cited : (49)

References (50)
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    • This result was confirmed by NOE studies performed on the cyclic diastereoisomers A and B. These compounds were smoothly prepared from the 80:20 mixture of 17a and 17b by sequential chemoselective hydrolysis of the tert-butyl ester group followed by cyclization with EDC and HOBT in DMF at room temperature, and finally separation by flash chromatography.
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    • At this moment in time the formation of a heptacoordinated complex (imine as a tridentate ligand) or, as widely reported for silicon, the formation of a hexacoordinated cationic complex, resulting from dissociation of a single chlorine ion cannot be excluded. For some examples of silicon complexes dealing with the latter hypothesis, see: (a) Denmark, S. E.; Stavenger, R. A. J. Am. Chem. Soc. 2000, 122, 8837. (b) Denmark, S. E.; Stavenger, R. A.; Wong, K. T.; Su, J. Am. Chem. Soc. 1999, 121, 4982 and references therein. (c) Short, J. D.; Attenoux, S.; Berrisford, D. J. Tetrahedron Lett. 1997, 38, 2351.
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    • note
    • It should be noted that the numbering scheme of 1 in Supporting Information is arbitrary, and that C-9 in the diagram corresponds to C-2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.