Alkoxide-Directed Hydride Addition to α,β-Unsaturated Sultones

Metz, Peter; Dawood, Kamal M.; Bramborg, Andrea; Darweesh, Ahmed F.; Spinde, Katrin; Rogachev, V. G.; Jäger, Anne

doi:10.3987/com-15-s(t)64

Search citation statements

Order By: Relevance

Paper Sections

Select...

General Procedures For the Preparation Of But-3-enyl Prop-2-ene-1-sulfonate Derivatives (3ab)1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2018

2022

Publication Types

Select...

Article1

Book1

Relationship

Self Cite1

Independent1

Authors

Journals

Cited by 2 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 3a was prepared according the general procedure from prop-2-ene-1-sulfonyl chloride (1) (2.1g, 15 mmol), but-3-en-1-ol (2a) (1g, 13.86 mmol) and TEA (2 mL). Colorless oil Rf: 0.53 (Et2O/pentane; 1/1) 29 ; Yield (2.44g, 90%). 1 6,7-Dihydro-3H-1,2-oxathiepine 2,2-dioxide (4a).…”

Section: General Procedures For the Preparation Of But-3-enyl Prop-2-ene-1-sulfonate Derivatives (3ab)mentioning

confidence: 99%

Ring closing metathesis and metal-catalyzed cyclopropanation for the preparation of sultone derivatives

Ali¹,

Metz²

2018

Arkivoc

Self Cite

View full text Add to dashboard Cite

Ring closing metathesis (RCM) using Grubbs catalyst 2 nd generation as a catalyst was applied to prepare series of novel unsaturated sultones with high yields. Many attempts, were applied for the cyclopropanation of the allylic sultones by Simmon-smith cyclopropanation using diethyl zinc/diiodomethane or Zn-Cu/diiodomethane but in each case the corresponding cyclic adduct was not formed. A novel palladium or preferably rhodiumcatalyzed cyclopropanation of unsaturated sultones with ethyl diazoacetate was achieved by the transition metal-catalyzed transfer of a CH-CO2Et unit. The reaction was applied by a portion-wise addition of ethyl diazoacetate over 6h to a mixture of the sultones and palladium(II) acetate or rhodium(II) acetate dimer under low temperature (0-20 o C). The desired products of the cyclopropanation were achieved in each case, as a single diastereomer with 33-37% yield in the allylic sultones and 10% for vinylic sultone.

show abstract

Section: General Procedures For the Preparation Of But-3-enyl Prop-2-ene-1-sulfonate Derivatives (3ab)mentioning

confidence: 99%