73423-01-5Relevant articles and documents
Efficient synthesis of β-hydroxy-α-amino acid derivatives via direct catalytic asymmetric aldol reaction of α-isothiocyanato imide with aldehydes
Chen, Xiaohong,Zhu, Yin,Qiao, Zhen,Xie, Mingsheng,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
supporting information; experimental part, p. 10124 - 10129 (2010/11/19)
An easily available and efficient chiral N,N'-dioxide-nickel(II) complex catalyst has been developed for the direct catalytic asymmetric aldol reaction of α-isothiocyanato imide with aldehydes which produces the products in morderate to high yields (up to 98%) with excellent diastereo-(up to >99:1 d.r.) and enantioselectivities (up to >99% ee). A variety of aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldehydes were found to be suitable substrates in the presence of 2.5 mol% l-proline-derived N,N'-dioxide L5-nickel(II) complex. This process was air-tolerant and easily manipulated with available reagents. Based on experimental investigations, a possible transition state has been proposed to explain the origin of reactivity and asymmetric inductivity.
