2022
DOI: 10.1021/acs.orglett.2c03123
|View full text |Cite
|
Sign up to set email alerts
|

An Access to Highly Functionalized Dihydrobenzofuran Spirooxindole Scaffolds

Abstract: We have developed an efficient protocol for the construction of polycyclic dihydrobenzofuran spirooxindole scaffolds via base promoted cascade annulation of Morita− Baylis−Hillman (MBH) carbonates of isatins with ortho-hydroxychalcones or ortho-hydroxy-β-nitrostyrenes. The complex polycyclic compounds were conveniently synthesized in satisfactory yields and with high diastereoselectivity. This protocol provides a swift and convenient approach for the assembly of diverse highly functionalized dihydrobenzofuran … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1

Citation Types

0
5
0

Year Published

2023
2023
2024
2024

Publication Types

Select...
8
1

Relationship

5
4

Authors

Journals

citations
Cited by 21 publications
(5 citation statements)
references
References 54 publications
0
5
0
Order By: Relevance
“…On the basis of the current results and previous works [ 54 61 ], a reaction mechanism for the formation of the spiro[indoline-3,5'-[1,2]diazepines] has been proposed and is depicted in Scheme 5 . At first, MBH carbonates of isatin 2 is attacked at the α-position by the Lewis base to give the ammonium salt A with elimination of carbon dioxide and a tert -butoxide ion.…”
Section: Resultsmentioning
confidence: 72%
“…On the basis of the current results and previous works [ 54 61 ], a reaction mechanism for the formation of the spiro[indoline-3,5'-[1,2]diazepines] has been proposed and is depicted in Scheme 5 . At first, MBH carbonates of isatin 2 is attacked at the α-position by the Lewis base to give the ammonium salt A with elimination of carbon dioxide and a tert -butoxide ion.…”
Section: Resultsmentioning
confidence: 72%
“…Switching the metal salt from Mg(OTf) 2 to Mg(ClO 4 ) 2 led to a higher diastereoselectivity (entry 13, 99% yield, >20:1 dr. and 89% ee). Performing the reaction without L 3 -PioAdmMe/Mg-(ClO 4 ) 2 (entry 14) led to the formation of product 3a in 63% yield with 1:11 dr (same diastereoselectivity as Yan's work 10 ). In sharp contrast, conducting the reaction with Mg(ClO 4 ) 2 afforded the product 3a in 31% yield with >20:1 dr (entry 15), indicating that the metal salts have a great influence on the diastereoselectivity of this reaction.…”
mentioning
confidence: 57%
“…Benefiting from their stable configurations and adjustable chiral pocket, chiral N,N′-dioxide−metal complexes have been successfully applied in a number of cycloaddition reactions 8 and other asymmetric transformations. 9 Inspired by Yan's work 10 (Scheme 1c) and as part of our ongoing interests on the concise synthesis of enantioenriched chiral spiro-oxindole molecules, 11 we envisioned that a chiral N,N′-dioxide−metal complex Lewis acid catalyst was a potential promoter for the cascade reaction cascade annulation reaction of MBH maleimides of isatins with ortho-hydroxychalcones. Herein, we disclose our results along this line.…”
mentioning
confidence: 99%
“…In recent years, the readily available and multifunctionalized Morita–Baylis–Hillman adducts of isatins have been recognized as powerful synthons in many transformation and annulation reactions. 9,10 Therefore, many [3 + 2] and [3 + 3] cycloaddition reactions of MBH adducts of isatins have been subsequently developed. 11 However, the more challenging [4 + 3] cycloaddition with MBH adducts of isatins has been less developed, probably due to the lack of suitable electrophilic diene components.…”
Section: Introductionmentioning
confidence: 99%