85539-66-8Relevant academic research and scientific papers
Switching and Conformational Fixation of Amides Through Proximate Positive Charges
Bartuschat, Amelie L.,Wicht, Karina,Heinrich, Markus R.
supporting information, p. 10294 - 10298 (2015/09/01)
Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization. Taking charge of conformation: Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization.
Is an iodine atom almighty as a leaving group for Bu3SnH-mediated radical cyclization? The effect of a halogen atom on the 5-endo-trig radical cyclization of N-vinyl-α-halo amides
Tamura, Osamu,Matsukida, Hana,Toyao, Atsushi,Takeda, Yoshifumi,Ishibashi, Hiroyuki
, p. 5537 - 5545 (2007/10/03)
The effect of a halogen atom as a leaving group on Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-1-enyl) α-halo amides was examined. The cyclization of α-chloro amides occurred with a high degree of efficiency, whereas the corresponding α-iodo congeners gave only limited quantities of cyclization products. A detailed study revealed that these phenomena could be attributed to the initial conformations of α-halo amides. The cyclizing ability of α-iodo amides can be restored with Bu3SnCl or Bu3SnF as an additive. The cyclization of an α-iodo amide in the presence of Bu3SnF could be applied to a short-step synthesis of lycoranes featuring sequential 5-endo-trig and 6-endo-trig radical cyclizations.
The use of an iodine atom as a leaving group for Bu3SnH-mediated 5-endo-trig radical cyclization of α-halo amides is not recommended
Ishibashi,Matsukida,Toyao,Tamura,Takeda
, p. 1497 - 1499 (2007/10/03)
Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-1-enyl) α-chloro amides occurred with a high degree of efficiency, whereas the corresponding α-iodo congeners gave only limited quantities of the cyclization products. The cyclizing
CYCLIZATION OF α-HALOAMIDE WITH INTERNAL DOUBLE BOND BY USE OF THE LOW-VALENT METAL COMPLEX
Mori, Miwako,Oda, Izumi,Ban, Yoshio
, p. 5315 - 5318 (2007/10/02)
The α-haloamide having internal double bond was allowed to react with a catalytic amount of Pd(PPh3)4 in the presence of proton sponge to produce a cyclized product in a fairly good yield possibly through the intermediation of ?-alkylmetal complex althoug
