10015-16-4Relevant academic research and scientific papers
Harnessing the Power of the Asymmetric Grignard Synthesis of Tertiary Alcohols: Ligand Development and Improved Scope Exemplified by One-Step Gossonorol Synthesis
Gilheany, Declan G.,Kavanagh, Saranna E.
, p. 8198 - 8203 (2020)
A series of N-substituted cyclohexyldiaminophenolic ligands for the asymmetric Grignard synthesis of tertiary alcohols is reported. The 2,5-dimethylpyrrole-decorated ligand led to improved enantioselectivities and broadened the scope of the methodology. As an exemplar, we report an unprecedented highly selective one-step synthesis of gossonorol in 93% ee, also constituting the shortest formal syntheses of natural products boivinianin B and yingzhaosu C.
The Importance of Resonance Stabilization in the Benzylic Solvolysis. Substituent Effects on the Solvolysis of α,α-Diisopropylbenzyl Chlorides
Fujio, Mizue,Nakata, Kazuhide,Kuwamura, Takashi,Nakamura, Hirotaka,Saeki, Yoshihiro,et al.
, p. 8309 - 8312 (2007/10/02)
The substituent effect on the solvolysis of α,α-diisopropylbenzyl chlorides can be described in terms of ?+ value.No significant steric loss of resonance was observed by introducing two bulky isopropyl groups into benzylic reaction center.
