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Volumn 48, Issue 34, 2009, Pages 6293-6295

Rhodium-catalyzed asymmetric enyne cycloisomerization of terminal alkynes and formal total synthesis of (-)-platensimycin

Author keywords

Asymmetric catalysis; Cycloisomerization; Platensimycin; Rhodium; Terminal alkynes

Indexed keywords

ASYMMETRIC CATALYSIS; BINAPHTHALENES; CYCLOISOMERIZATION; CYCLOISOMERIZATIONS; PLATENSIMYCIN; RHODIUM-CATALYZED; TERMINAL ALKYNE; TERMINAL ALKYNES; TOTAL SYNTHESIS;

EID: 70349895948     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901992     Document Type: Article
Times cited : (82)

References (34)
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    • 3, 600 MHz): 2a (E-isomer), δ = 6.28 (d, J= 12.0 Hz, 1H), 4.63 ppm (dd, J=11.9, 9.3 Hz, 1H); 2a′ (Z-isomer), δ = 6.32 (dd, J=5.7, 0.9 Hz, 1H), 4.19 ppm (dd, 7=8.4, 5.8 Hz, 1H).
    • 3, 600 MHz): 2a (E-isomer), δ = 6.28 (d, J= 12.0 Hz, 1H), 4.63 ppm (dd, J=11.9, 9.3 Hz, 1H); 2a′ (Z-isomer), δ = 6.32 (dd, J=5.7, 0.9 Hz, 1H), 4.19 ppm (dd, 7=8.4, 5.8 Hz, 1H).
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    • A closely related terminal alkynyl-ene substrate was reported in reference [3d] to undergo a rapid cyclization (< 5 min, 100% conversion) in the presence of a catalytic system generated in situ by sequential mixing of, Rh(cod)Cl}2, S)-binap, substrate (1 min, and AgSbF 6 in DCE at room temperature to afford a related product in poor enantioselectivity (i.e. 6.5% ee, see experimental and footnote 14c in reference [3d, The key to the success of our protocol is the use of preformed, more well-defined catalyst [Rh, S)-binap)]SbF6. The precise mechanistic differences between the two catalytic systems, however, remain to be elucidated, although the undefined nature of the catalytic species in reference [3d] and the slower reaction rates (12-16 h reaction times at room temperature) under our reaction conditions may be important factors
    • 6. The precise mechanistic differences between the two catalytic systems, however, remain to be elucidated, although the undefined nature of the catalytic species in reference [3d] and the slower reaction rates (12-16 h reaction times at room temperature) under our reaction conditions may be important factors.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.