505-92-0Relevant articles and documents
Lewis Base/Br?nsted Acid Co-Catalyzed Asymmetric Thiolation of Alkenes with Acid-Controlled Divergent Regioselectivity
Luo, Hui-Yun,Dong, Jia-Wei,Xie, Yu-Yang,Song, Xu-Feng,Zhu, Deng,Ding, Tongmei,Liu, Yuanyuan,Chen, Zhi-Min
supporting information, p. 15411 - 15418 (2019/11/14)
A divergent strategy for the facile preparation of various enantioenriched phenylthio-substituted lactones was developed based on Lewis base/Br?nsted acid co-catalyzed thiolation of homoallylic acids. The acid-controlled regiodivergent cyclization (6-endo vs. 5-exo) and acid-mediated stereoselective rearrangement of phenylthio-substituted lactones were explored. Experimental and computational studies were performed to clarify the origins of the regioselectivity and enantioselectivity. The calculation results suggest that C?O and C?S bond formation might occur simultaneously, without formation of a commonly supposed catalyst-coordinated thiiranium ion intermediate and the potential π–π stacking between substrate and SPh as an important factor in the enantio-determining step. Finally, this methodology was applied in the rapid syntheses of the bioactive natural products (+)-ricciocarpin A and (R)-dodecan-4-olide.
ONE-POT SYNTHESIS OF (Z)-4-ALKENOIC ACIDS
Fujisawa, Tamotsu,Sato, Toshio,Kawara, Tatsuo,Naruse, Kouichi
, p. 1123 - 1124 (2007/10/02)
The reaction of β-propiolactone with di-(Z)-1-alkenylcuprates, prepared from Grignard reagents, copper(I) iodide and acetylene, gave (Z)-4-alkenoic acids in high yields in one-pot operation.
