Aalto University School of Science and Technology, Faculty of Chemistry and Materials Sciences, Department of Chemistry, P.O. Box 16100, FI-00076 Aalto, Finland.
Org Lett. 2010 Mar 19;12(6):1145-7. doi: 10.1021/ol100037c.
The mildness and low basicity of vinylzinc species functioning as a nucleophile in addition to alpha-chiral aldehydes is characterized by lack of epimerization of the vulnerable stereogenic center. This is demonstrated by a highly diastereoselective synthesis of 1-deoxygalactonojirimycin in eight steps from commercial starting materials with overall yield of 35%.
作为亲核试剂的乙烯基锌物种的温和性和低碱性，加上α-手性醛，其特点是脆弱的立体中心不易发生差向异构化。这一点通过从商业起始原料出发，经过 8 步反应，以 35%的总收率，高非对映选择性地合成了 1-脱氧半乳糖基乔来眯，得到了很好的证明。
