Alcohols in Isonitrile‐Based Multicomponent Reaction: Passerini Reaction of Alcohols in the Presence of <i>O</i>‐Iodoxybenzoic Acid

2005, Multicomponent Reaction

Passerini M., 1921, Gazz. Chim. Ital., 51, 126

Passerini M., 1922, Gazz. Chim. Ital., 52, 432

Banfi L., 2005, Org. React., Vol. 65, 1

Dömling A., 2000, Angew. Chem., 112, 3301, 10.1002/1521-3757(20000915)112:18<3300::AID-ANGE3300>3.0.CO;2-Z

10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U

10.2174/0929867033368600

10.1055/s-2003-40507

10.1002/ejoc.200390167

10.1021/cr0505728

10.1021/ar050113t

10.1002/1521-3757(20010803)113:15<2893::AID-ANGE2893>3.0.CO;2-F

10.1002/1521-3773(20010803)40:15<2812::AID-ANIE2812>3.0.CO;2-X

10.1039/a903980e

10.1021/jo00127a036

For other applications of IBX see:

10.1002/(SICI)1521-3757(20000204)112:3<636::AID-ANGE636>3.0.CO;2-F

10.1002/(SICI)1521-3773(20000204)39:3<625::AID-ANIE625>3.0.CO;2-#

10.1002/1521-3757(20010105)113:1<208::AID-ANGE208>3.0.CO;2-Z

10.1002/1521-3773(20010105)40:1<202::AID-ANIE202>3.0.CO;2-3

10.1002/1521-3757(20021104)114:21<4216::AID-ANGE4216>3.0.CO;2-K

10.1002/1521-3773(20021104)41:21<4059::AID-ANIE4059>3.0.CO;2-R

10.1021/ja0400382

For tandem oxidation/Wittig reactions initiated by Dess–Martin periodinane (DMP) or IBX see:

10.1002/jlcr.2580240609

10.1021/jo971569u

10.1055/s-1999-2550

10.1021/ol026427n

10.1021/jo9824596

Plumb J. B., 1990, Chem. Eng. News, 68, 29

IBX is able to oxidize THF at elevated temperatures (80 °C and above); see references [9b] and [11].

Passerini M., 1921, Gazz. Chim. Ital., 51, 181

Oxidation of5 iwith IBX (in THF or DMSO) or under Swern conditions led only to the decomposition of the starting material.

For a few diastereoselective P‐3CRs see:

10.1021/jo026614z

Frey R., 2003, Synlett, 1536

10.1016/j.tet.2004.03.084

For enantioselective P‐3CRs see:

10.1021/ja035410c

10.1021/ol035010u

10.1021/ol0482893

Experimental procedures product characterization and1H and13C NMR spectra of1 a–1 uare provided in the Supporting Information.