226984-53-8Relevant academic research and scientific papers
O2-Assisted Four-Component Reaction of Vinyl Magnesium Bromide with Chiral N-tert-Butanesulfinyl Imines To Form syn-1,3-Amino Alcohols
Gao, Lu,Luo, Jingfan,Song, Zhenlei,Wang, Runping,Zhang, Hongyun,Zheng, Chunmei
, p. 24644 - 24649 (2021/10/12)
An O2-assisted, four-component reaction has been developed to synthesize a wide range of syn-1,3-amino alcohols in one step. The reaction proceeds by oxygenation of vinyl magnesium bromide (component-I) with O2 (component-II) to give
Catalytic Aza-Wacker Annulation: Tuning Mechanism by the Activation Mode of Amide and Enantioselective Syntheses of Melinonine-E and Strychnoxanthine
Xie, Changmin,Luo, Jisheng,Zhang, Yuping,Huang, Sha-Hua,Zhu, Lili,Hong, Ran
supporting information, p. 2386 - 2390 (2018/04/30)
An unprecedented N-substituent of the amide was found to be crucial for the successful annulation to establish 2-azabicyclo[3.3.1]nonane and other ring skeletons in good yield. The novel catalytic aza-Wacker annulation methodology was further illustrated
An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives
Xu, Jun,Tong, Rongbiao
, p. 2952 - 2956 (2017/07/24)
An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.
Aziridine-allylsilane-mediated total synthesis of (-)-yohimbane
Bergmeier, Stephen C.,Seth, Punit P.
, p. 3237 - 3243 (2007/10/03)
A total asymmetric synthesis of (-)-yohimbane and ent-alloyohimbane is reported. The synthesis utilizes a novel aziridine-allylsilane cyclization reaction as a key step in the synthesis. Treatment of optically pure aziridine-allylsilane 16 with BF3 · OEt2 provided a mixture of aminomethyl substituted carbocycles trans-20a and cis-20b in excellent yield and modest diastereoselectivity (trans/cis 3:1). Alkylation of the tosylamide followed by oxidation of the olefin in 20 provided the lactam 38, which was converted to (-)-yohimbane and ent-alloyohimbane by a Bischler-Napieralski reaction. The synthesis provided (-)-yohimbane in eight steps and 24% overall yield (from 16).
