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Volumn 129, Issue 6, 2007, Pages 1522-1523

Enantioselective synthesis of planar-chiral metacyclophanes through rhodium-catalyzed alkyne cyclotrimerization

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CYCLOPHANE DERIVATIVE; METACYCLOPHANE DERIVATIVE; RHODIUM COMPLEX;

EID: 33846953245     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0679127     Document Type: Article
Times cited : (83)

References (36)
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    • (2004) Modern Cyclophane Chemistry
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    • Vögtle, F, Ed, Wiley: Chichester, UK
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    • For a review of the cyclophane synthesis, see
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    • For a recent example of the synthesis and resolution of planar-chiral [n]-paracyclophanes, see: Ueda, T.; Kanomata, N.; Machida, H. Org. Lett. 2005, 7, 2365-2368.
    • For a recent example of the synthesis and resolution of planar-chiral [n]-paracyclophanes, see: Ueda, T.; Kanomata, N.; Machida, H. Org. Lett. 2005, 7, 2365-2368.
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    • For our synthesis of cyclophanes through Rh-catalyzed alkyne cyclotrimerization, see: a
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    • Synthesis of cyclophanes via transition-metal-catalyzed [2 + 2 + 2] cycloaddition: Co: (a) Boñaga, L. V. R.; Zhang, H.-C.; Moretto, A. F.; Ye, H.; Gautheir, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. J. Am. Chem. Soc. 2005, 127, 3473-3485.
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    • For our synthesis of axially chiral compounds through Rh-catalyzed enantioselective alkyne cyclotrimerization, see: (a) Tanaka, K, Nishida, G, Wada, A, Noguchi, K. Angew. Chem, Int. Ed. 2004, 43, 6510-6512
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  • 27
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    • For the synthesis of planar-chiral [n]metacyclophanes, see: (a) Piatek, P.; Kalisiak, J.; Jurczak, J. Tetrahedron Lett. 2004, 45, 3309-3311.
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    • Results with other BINAP-type ligands: BINAP (9% yield, 91% ee), xyl-BINAP (15% yield, 83% ee), Segphos (7% yield, 26% ee).
    • Results with other BINAP-type ligands: BINAP (9% yield, 91% ee), xyl-BINAP (15% yield, 83% ee), Segphos (7% yield, 26% ee).
  • 36
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    • The reaction of 8h by using high catalyst loading (10 mol % of Rh) did not improve the yields of cyclophanes significantly (9h: 24% yield, 10h: 17% yield).
    • The reaction of 8h by using high catalyst loading (10 mol % of Rh) did not improve the yields of cyclophanes significantly (9h: 24% yield, 10h: 17% yield).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.