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Volumn 39, Issue 44, 1998, Pages 8175-8178

Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

Author keywords

Diastereoselection; Enantioselection; Epoxidation; Rearrangements

Indexed keywords

AMIDE; CYCLOPENTENE DERIVATIVE; LITHIUM; OXIDE;

EID: 0032578812     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01821-8     Document Type: Article
Times cited : (19)

References (37)
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    • 17. To the best of our knowledge, only three diprotected amines 1 have previously been prepared and in two cases the nitrogen was part of a heterocyclic base. See: Zhou, J.; Bouhadir, K.; Webb, T. R.; Shevlin, P. B. Tetrahedron Lett. 1997, 38, 4037-4038 and references 12 and 13 above.
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    • N-Boc protected sulfonamides 18 (93% yield) and 19 (86% yield) were prepared from the corresponding sulfonamides according to a literature procedure
    • 23. N-Boc protected sulfonamides 18 (93% yield) and 19 (86% yield) were prepared from the corresponding sulfonamides according to a literature procedure: Neustadt, B. R. Tetrahedron Lett. 1994, 35, 379-380.
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    • Deprotection of either protecting group in N-diprotected alkene 21 was easy. Boc deprotection using TFA or sulfonamide deprotection using mercaptoacetic acid (according to Fukuyama's procedure reported in reference 18) gave the N-monoprotected alkenes (each in quantitative yield)
    • 24. Deprotection of either protecting group in N-diprotected alkene 21 was easy. Boc deprotection using TFA or sulfonamide deprotection using mercaptoacetic acid (according to Fukuyama's procedure reported in reference 18) gave the N-monoprotected alkenes (each in quantitative yield).
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    • note
    • δH (CHO) values: 3.47 for cis-26, 3.57 for trans-26.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.