220306-70-7Relevant academic research and scientific papers
Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates
Banerjee, Amit,Hattori, Tomohiro,Yamamoto, Hisashi
, (2021/06/16)
Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).
‘Double chiral’ new members of calixsalen family
Petryk, Ma?gorzata,Janiak, Agnieszka,Kwit, Marcin
, p. 1373 - 1383 (2017/10/31)
Synthesis and X-ray diffraction studies on the first examples of ‘double chiral’ calixsalens are presented. In these molecules, one can clearly distinguish two chiral zones. The first one is made by the macrocycle base, whereas the second chiral zone is s
