99440-25-2

Upstream product

• 111931-30-7 (S)-3-(3,3-Dimethyl-cyclohex-1-enylmethyl)-4-isopropyl-2-methylene-oxazolidine 

Downstream Products

• 111931-32-9 Methanesulfonic acid 2-((S)-2,2-dimethyl-6-methylene-cyclohexyl)-ethyl ester 
• 83631-17-8 (+)-dihydropallescensin-2 
• 782474-36-6 ((S)-2,2-Dimethyl-6-methylene-cyclohexyl)-acetic acid 
• 112243-60-4 (1'S)-2-(2',2'-dimethyl-6'-methylene-cyclohexyl)-ethanol 
• 111931-31-8 (S)-2-(2-Iodo-ethyl)-1,1-dimethyl-3-methylene-cyclohexane 
• 98876-73-4 C₁₇H₃₀NO⁽¹⁺⁾*CH₃O₄S^(1-) 

Relevant academic research and scientific papers

ASYMMETRIC AZA-CLAISEN REARRANGEMENT: SYNTHESIS OF (+)-DIHYDROPALLESCENSIN-2

Synthetic confirmation of the C(1')-(S)-configuration of (+)-dihydropallescensin-2 (1) is reported, the key reaction being a chiron-mediated asymmetric aza-Claisen rearrangement (67).

Enantioselective Preparation of 3-Substituted-4-pentenoic Acids via the Claisen Rearrangement

Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 4 is described.The starting materials, allylic alkylating agant 1 and optically pure oxazoline 2, are easily prepared and, in a one-pot procedure, generate rearranged oxazolines 5 in 52-94percent diastereomeric excess.The overall chemical yields for 2 -> 5 range from 51 to 78percent.The aza-Claisen rearrangement (4 -> 5) proceeds with excellent N,O-acetal face selectivity and with good to excellent chair selectivity.Hydrolysis of rearranged oxazoline 5 completes an enantioselective synthesis of 3-substituted pent-4-enoic acids.