52890-22-9Relevant academic research and scientific papers
An efficient protocol for the cross-metathesis of sterically demanding olefins
Wang, Zhen J.,Jackson, W. Roy,Robinson, Andrea J.
supporting information, p. 3006 - 3009 (2013/07/26)
Cross-metathesis of a wide range of previously unreactive, sterically demanding alkenes can be achieved in fair to excellent yield using a commercially available catalyst by a facile strategy involving reversal of steric preference.
Efficient carboazidation of alkenes using a radical desulfonylative azide transfer process
Weidner, Karin,Giroult, Andre,Panchaud, Philippe,Renaud, Philippe
supporting information; experimental part, p. 17511 - 17515 (2011/02/23)
The radical-mediated carboazidation of terminal alkenes using electrophilic alkanesulfonyl azides is reported. A single reagent delivers the necessary electrophilic alkyl radical as well as the azido group, and good yields are obtained by using a moderate excess of the carboazidating reagent (1.5-2 equiv). Interestingly, in addition to the starting sulfonyl azide, this method requires only the use of a radical initiator, di-tert-butyldiazene. In terms of atom economy, this azide transfer reaction is close to ideal, as SO2 (1 equiv) is the only side product. The synthetic potential of this process has been demonstrated by a formal synthesis of the alkaloid lepadiformine C.
Total synthesis of the marine alkaloid (±)-lepadiformine via a radical carboazidation
Schaer, Pascal,Renaud, Philippe
, p. 1569 - 1571 (2007/10/03)
The total synthesis of lepadiformine has been achieved in 10 steps and 15% overall yield from cyclohexanone. The amino-substituted quaternary carbon center is created through a radical carboazidation reaction. The tricyclic core of lepadiformine is built via an efficient hydrogenation process, involving reduction of the azide and intramolecular reductive amination of a ketone, followed by lactamization of the intermediate γ-aminoester. The hydroxymethyl side chain is introduced according to a modified Takahata procedure after conversion of the lactam into a thiolactam.
Epoxide-Initiated Cationic Cyclization of Azides: A Novel Method for the Stereoselective Construction of 5-Hydroxymethyl Azabicyclic Compounds and Application in the Stereo- and Enantioselective Total Synthesis of (+)- and (-)-Indolizidine 167B and 209D
Reddy, P. Ganapati,Baskaran, Sundarababu
, p. 3093 - 3101 (2007/10/03)
A novel and general method has been developed for the stereoselective construction of 5-hydroxymethyl azabicyclic ring skeletons based on epoxide-initiated cationic cyclization of azides. The key cyclization reaction was systematically studied with the mo
Epoxide-initiated electrophilic cyclization of azides: A novel route for the stereoselective construction of azabicyclic ring systems and total synthesis of (±)-indolizidine 167B and 209D
Reddy, P. Ganapati,Varghese, Babu,Baskaran, Sundarababu
, p. 583 - 585 (2007/10/03)
(Matrix presented) A novel and general method for the stereoselective construction of 5-hydroxymethyl azabicyclic ring skeletons based on epoxide initiated electrophilic cyclization of azides has been developed and applied in the synthesis of (±)-indolizi
Synthetic studies on the perhydropyrrolo[2,1-j]quinoline marine alkaloids lepadiformine and cyclindricine C using a 2-azapentadienyl anion cycloaddition. Synthesis of 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C)
Pearson, William H.,Barta, Nancy S.,Kampf, Jeff W.
, p. 3369 - 3372 (2007/10/03)
Tin-lithium exchange of 13 with n-BuLi produced the 2-azapentadienyl anion 6 (R = CH3), which participated in a [π4s+π2s] cycloaddition reaction with phenyl vinyl sulfide to afford the spirocyclic pyrrolidine 14, which as coverted to 2,13-diepi
CARBONYL METHYLENATION OF EASILY ENOLIZABLE KETONES
Hibino, Jun-ichi,Okazoe, Takashi,Takai, Kazuhiko,Nozaki, Hitosi
, p. 5579 - 5580 (2007/10/02)
An organometallic reagent prepared from CH2I2, Zn, and TiCl4 is effective for methylenation of the title ketones.
