Boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols

2019 ◽  
Vol 17 (7) ◽  
pp. 1901-1905 ◽  
Author(s):  
Hongqing Yao ◽  
Jiawei Liu ◽  
Chuan Wang
Keyword(s):  
Boronic Acid ◽  
Ring Opening ◽  
Selective Ring Opening ◽  
Epoxy Alcohols

A boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols as nucleophiles has been accomplished.

Construction the A-B bicyclic ring structure of Stemocurtisisne

2020 ◽  
Vol 17 ◽  
Author(s):  
Duc Dau Xuan
Keyword(s):  
Glutamic Acid ◽  
Natural Product ◽  
Mannich Reaction ◽  
Boronic Acid ◽  
Ring Opening ◽  
Ring Structure ◽  
Starting Material ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

: The synthesis of the A-B bicyclic ring structure 3 of the natural product Stemocurtisine is described. The synthesis was accomplished in seven synthetic steps from commercially available L-glutamic acid. The key step involved a borono-Mannich reaction between the hemiaminal 6 and trans-β-styryl boronic acid and trans-β-styrylpotassiumtrifluoroborate to prepare the cis diene 4. Attempts to prepare the A-B-C ring compound 2 via intramolecular epoxide ring opening followed by rearangement under different basic conditions were unsuccessful. Only unreactive starting material was recovered.

S ‐Carboxyanhydrides: Ultrafast and Selective Ring‐Opening Polymerizations Towards Well‐defined Functionalized Polythioesters

2021 ◽  
Vol 133 (19) ◽  
pp. 10893-10900
Author(s):  
Yanchao Wang ◽  
Maosheng Li ◽  
Shixue Wang ◽  
Youhua Tao ◽  
Xianhong Wang
Keyword(s):  
Ring Opening ◽  
Selective Ring Opening

ChemInform Abstract: NEIGHBORING GROUP EFFECTS IN EPOXIDE RING OPENING, CIS-EPOXY-ALCOHOLS

1976 ◽  
Vol 7 (42) ◽  
pp. no-no
Author(s):  
ERWIN GLOTTER ◽  
PNINA KRINSKY ◽  
MIRIAM REJTOE ◽  
MARTIN WEISSENBERG
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Neighboring Group ◽  
Epoxide Ring Opening ◽  
Epoxy Alcohols ◽  
Group Effects

C3-Allylation of Indoles via an Iridium-Catalyzed Branch-Selective Ring-Opening Reaction of Vinylcyclopropanes

Synthesis ◽  
2018 ◽  
Vol 51 (07) ◽  
pp. 1655-1661 ◽  
Author(s):  
Guang-Jian Mei ◽  
Feng Shi ◽  
Lei Yu ◽  
Zi-Qi Zhu ◽  
Meng Sun
Keyword(s):  
Ring Opening ◽  
Economic Approach ◽  
Whole Process ◽  
Ring Opening Reaction ◽  
Selective Ring Opening

An iridium-catalyzed branch-selective ring-opening reaction of vinylcyclopropanes with indoles has been established, which afforded C3-allylindoles in generally good to excellent yields (up to 95%). Considering that no wastes were generated in the whole process and branch-selective ring-opening reaction of vinylcyclopropanes was rarely reported, this strategy not only can be regarded as a highly atom-economic approach for C3-allylindoles, but also will greatly enrich the chemistry of vinylcyclopropanes.

Sign in / Sign up

Export Citation Format

Share Document