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Volumn 50, Issue 47, 2011, Pages 11257-11260

Formation of isoxazolidines by enantioselective copper-catalyzed annulation of 2-nitrosopyridine with allylstannanes

Author keywords

asymmetric synthesis; copper; cycloadditions; heterocycles; rearrangements

Indexed keywords

ALKENYLSTANNANES; ASYMMETRIC SYNTHESIS; CYCLOADDITIONS; DIASTEREO- AND ENANTIOSELECTIVITY; ENANTIOSELECTIVE; ENANTIOSELECTIVIES; HETEROCYCLES; HIGH YIELD; ISOXAZOLIDINES; REARRANGEMENTS;

EID: 81255148078     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105515     Document Type: Article
Times cited : (46)

References (33)
  • 18
    • 81255128785 scopus 로고    scopus 로고
    • Review on nitroso-Diels-Alder reactions using acyl nitroso compounds
    • Review on nitroso-Diels-Alder reactions using acyl nitroso compounds:, B. S. Bodnar, M. J. Miller, Angew. Chem. 2011, 123, 5746
    • (2011) Angew. Chem. , vol.123 , pp. 5746
    • Bodnar, B.S.1    Miller, M.J.2
  • 32
    • 33847085986 scopus 로고
    • It seems that the pyridyl group might stabilize the intermediately formed cationic stannacyclopropane (see structure C in Scheme 2). In the reaction of the trans-allyltributylstannanes this interaction forces the substituent R to be placed next to the shielding phenyl group. This is likely the reason why a drop in selectivity was observed with trans-allyltributylstannanes with R substituents larger than methyl.: Y. Yamamoto, H. Yatagai, Y. Naruta, K. Maruyama, J. Am. Chem. Soc. 1980, 102, 7107.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 7107
    • Yamamoto, Y.1    Yatagai, H.2    Naruta, Y.3    Maruyama, K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.