Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
J Org Chem. 2011 Apr 1;76(7):2204-13. doi: 10.1021/jo200082w. Epub 2011 Mar 7.
New chiral α-chloro-β-amino-N-sulfinyl imidates were synthesized in high yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of (R(S))-methyl N-tert-butanesulfinyl-2-chloroethanimidate with aromatic aldimines. The α-chloro-β-amino-N-sulfinylimidates proved to be excellent building blocks for the asymmetric synthesis of β-amino-α-chloro amides and esters, aziridine-2-carboxylic amides and esters, trans-2-aryl-3-chloroazetidines, and methyl 4-phenyloxazolidin-2-one-5-carboxylate. The obtained absolute anti-diastereoselectivity is the opposite of the stereochemical outcome observed for α-methyl-substituted imidates.
新型手性 α-氯-β-氨基-N-亚磺酰基亚氨基酯通过（R(S））-甲基 N-叔丁基亚磺酰基-2-氯乙亚氨酸酯与芳族亚胺的高反选择性 Mannich 型反应以高产率和优异的非对映过量合成。α-氯-β-氨基-N-亚磺酰基亚氨基酯被证明是不对称合成β-氨基-α-氯酰胺和酯、氮杂环丙烷-2-甲酰胺和酯、反式-2-芳基-3-氯氮杂环丁烷和甲基 4-苯恶唑烷-2-酮-5-羧酸酯的优异构建块。获得的绝对非对映选择性与观察到的 α-甲基取代亚氨基酯的立体化学结果相反。
