Organocatalytic Asymmetric Sequential 1,6-Addition/Acetalization of 1-Oxotetralin-2-carbaldehyde to ortho-Hydroxyphenyl-Substituted para-Quinone Methides for Synthesis of Spiro-3,4-dihydrocoumarins

• DOI: 10.1021/acs.joc.7b03177
• Publication Date: 2018-02-06T18:44:23Z
• Authors: Zhi-Pei Zhang; Li Chen; Xin Li; Jin-Pei Cheng
• Keywords: Squaramide

A chiral squaramide catalyzed approach constructing spiro-3,4-dihydrocoumarin motif by the enantioselective 1,6-addition/acetalization reactions of 1-oxotetralin-2-carbaldehydes and ortho-hydroxyphenyl-substituted para-quinone methides followed an oxidation was developed. The proceeded smoothly with a wide range p-QMs to generate corresponding products in high yields excellent diastereoselectivities (>19:1 dr) enantioselectivities (up 99% ee).