Details

Autor(en) / Beteiligte

• Zhang, Zhi-Pei
• Chen, Li
• Li, Xin
• Cheng, Jin-Pei

Titel

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

Ist Teil von

• Journal of organic chemistry, 2018-03, Vol.83 (5), p.2714-2724

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 by an oxidation was developed. The reactions proceeded smoothly with a wide range of p-QMs and 1-oxotetralin-2-carbaldehydes to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee).