Organic Letters 2011-09-02

Stereoselective synthesis of substituted 1,3-oxazolidines via Pd-catalyzed carboamination reactions of O-vinyl-1,2-amino alcohols.

Amanda F Ward, John P Wolfe

Index: Org. Lett. 17th ed., 13 , 4728-4731, (2011)

Full Text: HTML

Abstract

The stereoselective synthesis of 2,4- and 2,5-disubstituted 1,3-oxazolidines is accomplished via Pd-catalyzed carboamination of O-vinyl-1,2-amino alcohol derivatives. The transformations generate cis-disubstituted products with good to excellent diastereoselectivity, and enantiomerically enriched substrates are converted without loss of optical purity. In addition to yielding synthetically useful products that are difficult to generate with existing methods, these transformations illustrate that electron-rich enol ethers are viable substrates for alkene carboamination processes.

Related Compounds

  • Vinylboronic anhyd...

Related Articles:

Transition metal-catalyzed synthesis and reactivity of N-alkenyl aziridines.

2005-03-17

[Org. Lett. 6th ed., 7 , 1161-1164, (2005)]

Stereoselective isomerisation of N-allyl aziridines into geometrically stable Z enamines by using rhodium hydride catalysis.

2008-01-01

[Chemistry 3rd ed., 14 , 886-894, (2008)]

The alkyl-connected 2-amino-6-vinylpurine (AVP) crosslinking agent for improved selectivity to the cytosine base in RNA

2010-01-01

[Bioorg. Med. Chem. 8th ed., 18 , 2894-2901, (2010)]

Kinetic resolution of axially chiral 2,2'-dihydroxy-1,1'-biaryls by palladium-catalyzed alcoholysis.

2005-08-03

[J. Am. Chem. Soc. 30th ed., 127 , 10474-10475, (2005)]

Efforts toward distorted spiropentanes.

2010-11-05

[J. Org. Chem. 21th ed., 75 , 7494-7497, (2010)]

More Articles...