161260-69-1

Basic information

• Product Name: (E)-(S)-2-Hydroxy-4-phenyl-but-3-enoic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
• Synonyms: (E)-(S)-2-Hydroxy-4-phenyl-but-3-enoic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
• CAS NO: 161260-69-1
• Molecular Weight: 290.316
• Mol File: 161260-69-1.mol

Chemical Properties

• CAS DataBase Reference: (E)-(S)-2-Hydroxy-4-phenyl-but-3-enoic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(S)-2-Hydroxy-4-phenyl-but-3-enoic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester(161260-69-1)
• EPA Substance Registry System: (E)-(S)-2-Hydroxy-4-phenyl-but-3-enoic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester(161260-69-1)

Safety Data

• Hazardous Substances Data: 161260-69-1(Hazardous Substances Data)

Upstream product

• 153062-67-0 (3R)-3-(4,4-dimethyl-2-oxotetrahydrofuranyl) (E)-2-diazo-4-phenyl-3-butenoate 

Downstream Products

• 129990-77-8 (2S)-2-Hydroxy-4-phenylbutyric acid methyl ester 
• 115016-95-0 (S)-2-hydroxy-4-phenylbutanoic acid 

Relevant articles and documents

Chiral catalyst enhancement of diastereocontrol for O-H insertion reactions of styryl- and phenyldiazoacetate esters of pantolactone

The chiral dirhodium(II) catalyst Rh2(MEAZ)4 increases diastereocontrol for intermolecular O-H insertion reactions of diazo esters having a chiral auxiliary over that achieved with Rh2(OAc)4.

A Stereospecific Access to Allylic Systems Using Rhodium(II)-Vinyl Carbenoid Insertion into Si-H, O-H, and N-H Bonds

Rhodium-catalyzed decomposition of α-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding α-silyl, α-hydroxy, α-alkoxy, α-amino, and α-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral α-vinyldiazoesters and Doyle's chiral catalyst Rh2(MEPY)4. In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh2(MEPY)4-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.

Rhodium(II)-vinylcarbenoid insertion into the Si - H bond. A new stereospecific synthesis of allylsilanes

Rh2(OAc)4 catalysed decomposition of vinyldiazocarbonyl compounds in the presence of organosilanes led stereospecifically to the corresponding allylsilanes in good yields. An asymmetric approach has also been considered as well as the extension of the methodology to the synthesis of other allylic systems.