ethyl (1S,5S)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate

Base Information

• Chemical Name: ethyl (1S,5S)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate
• CAS No.: 1228457-89-3
• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.317

Synonyms:ethyl (1S,5S)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate

Chemical Property of ethyl (1S,5S)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate

Chemical Property:

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Technology Process of ethyl (1S,5S)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate

There total 6 articles about ethyl (1S,5S)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

ethyl (E)-2,5-dimethyl-3,4-dioxo-6-phenylhex-5-enoate (1228457-75-7) → ethyl (1S,5S)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate (1228457-89-3)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (1R,7R)-9,9-dimethyl-4-(N-phenyl-2-pyridylamino)-2,2,6,6-tetraphenyl-3,5,8,10-tetraoxa-4-phosphabicyclo[5.3.0]decane; In acetonitrile; at 20 ℃; for 6h; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/anie.201500881

Reference yield:

ethyl (E)-2,5-dimethyl-3,4-dioxo-6-phenylhex-5-enoate (1228457-75-7) → ethyl (1S,5S)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate (1228457-89-3) + ethyl (1R,5R)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate

Guidance literature:

With C₃₁H₂₃F₆N₃S; In toluene; at 20 ℃; for 168h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ja103028r

Reference yield:

C16H18O4 → ethyl (1S,5S)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate (1228457-89-3) + ethyl (1R,5R)-3-hydroxy-1,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarboxylate

Guidance literature:

With C₃₁H₂₃F₆N₃S; In toluene; at 23 ℃; Overall yield = 67 %; enantioselective reaction;

DOI:10.1021/jacs.5b08969

upstream raw materials:

ethyl (E)-2,5-dimethyl-3,4-dioxo-6-phenylhex-5-enoate

2-methyl-3-phenylacrylic acid

(E)-2-methyl-3-phenylacryloyl chloride

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