154659-29-7Relevant academic research and scientific papers
Pinacol cross coupling of 2-[N-(alkoxycarbonyl)amino] aldehydes and aliphatic aldehydes by [V2Cl3(THF)6]2[Zn2Cl 6]. Synthesis of syn,syn-3-[N-(alkoxycarbonyl)amino] 1,2-diols
Konradi, Andrei W.,Kemp, Scott J.,Pedersen, Steven F.
, p. 1316 - 1323 (1994)
Slow addition of 2-[N-(alkoxycarbonyl)amino] aldehydes to mixtures of [V2Cl3(THF)6]2[Zn2Cl 6] and aliphatic aldehydes gave syn,syn-3-[N-(alkoxycarbonyl)amino] 1,2-diols in good yield and high enantiomeric purity (>99:1). The alkyl group of the N-alkoxycarbonyl was shown to influence the yield: Me > allyl > Bn > t-Bu. Only the syn,syn diastereomer was observed (>20:1), except with N-Cbz-alaninal (10:1:1), O-benzyl-N-Cbz-serinal (7:1), and N-Cbz-prolinal (5:1 to 12:1). A new serinai derivative, N-Cbz-O-TBS-serinal, was cross coupled with n-pentadecanal to give a derivative of xylo-D-C18-phytosphingosine.
Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
, p. 10145 - 10149 (2016/08/16)
A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
