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Volumn 74, Issue 15, 2009, Pages 5652-5655

Expedite protocol for construction of chiral regioselectively N-protected monosubstituted piperazine, 1,4-diazepane, and 1,4-diazocane building blocks

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS; AMINOLYSIS; AZIRIDINES; BUILDING BLOCK; CHEMICAL EQUATIONS; CHROMATOGRAPHIC PURIFICATION; MITSUNOBU CYCLIZATION; SHORT REACTION TIME; SOLUTION PHASE SYNTHESIS; STEP SEQUENCES;

EID: 68049108398     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900441s     Document Type: Article
Times cited : (51)

References (55)
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    • For synthesis of tetraaza macrocycles bearing a chiral diazepane ring, see
    • For synthesis of tetraaza macrocycles bearing a chiral diazepane ring, see: Kang, S.-G.; Choi, J.-S.; Nam, K.; Chun, H.; Kim, K. Inorg. Chim. Acta 2004, 357, 2783-2790.
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  • 34
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    • For complete data on aziridine building blocks 2a-e, see ref 17c. For further details on aziridine 2f, see the Supporting Information
    • For complete data on aziridine building blocks 2a-e, see ref 17c. For further details on aziridine 2f, see the Supporting Information.
  • 35
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    • To avoid possible repeated ring-opening of aziridine building blocks by the secondary amine formed in the reaction, a large excess of the amino alcohol was used during the first step of the sequential protocol
    • To avoid possible repeated ring-opening of aziridine building blocks by the secondary amine formed in the reaction, a large excess of the amino alcohol was used during the first step of the sequential protocol.
  • 37
    • 68049098617 scopus 로고    scopus 로고
    • When diethyl azodicarboxylate (DEAD) was employed in this Fukuyama-Mitsunobu reaction, a similar yield was obtained. Cf.: Kümmerle, A. E. Synlett 2008, 2373-2374.
    • When diethyl azodicarboxylate (DEAD) was employed in this Fukuyama-Mitsunobu reaction, a similar yield was obtained. Cf.: Kümmerle, A. E. Synlett 2008, 2373-2374.
  • 38
    • 37549020046 scopus 로고    scopus 로고
    • For recent examples on Fukuyama-Mitsunobu reactions, see: a
    • For recent examples on Fukuyama-Mitsunobu reactions, see: (a) Nielsen, T. E.; Schreiber, S. L. Angew. Chem., Int. Ed. 2008, 47, 48-56.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 48-56
    • Nielsen, T.E.1    Schreiber, S.L.2
  • 42
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    • For complete optical rotation data, see the Supporting Information
    • For complete optical rotation data, see the Supporting Information.
  • 43
    • 43849094669 scopus 로고    scopus 로고
    • For recent examples on Fukuyama-Mitsunobu and Mitsunobu reactions with diols, see: a
    • For recent examples on Fukuyama-Mitsunobu and Mitsunobu reactions with diols, see: (a) Valeur, E.; Roche, D. Tetrahedron Lett. 2008, 49, 4182-4185.
    • (2008) Tetrahedron Lett , vol.49 , pp. 4182-4185
    • Valeur, E.1    Roche, D.2
  • 47
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    • For a recent investigation on SPS of medium-sized as well as very large rings, see
    • For a recent investigation on SPS of medium-sized as well as very large rings, see: Bisegger, P.; Manov, N.; Bienz, S. Tetrahedron 2008, 64, 7531-7536.
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    • Bisegger, P.1    Manov, N.2    Bienz, S.3
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    • 13C NMR signals were doubled indicating the presence of two rotamers involving the carbamate group. For further details, see the Supporting Information.
    • 13C NMR signals were doubled indicating the presence of two rotamers involving the carbamate group. For further details, see the Supporting Information.
  • 55
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    • For further details, see the Experimental Section
    • For further details, see the Experimental Section.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.