+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on Google+Follow on Google+
Follow on LinkedInFollow on LinkedIn

+ Translate

Regioselective hydroformylation of allylic alcohols

Regioselective hydroformylation of allylic alcohols

Organic Letters 13(10): 2686-2689

A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO and hydrogen.

(PDF same-day service: $19.90)

Accession: 055445677

Download citation: RISBibTeXText

PMID: 21504208

DOI: 10.1021/ol200782d

Related references

Metal-Free Catalyzed Regioselective Allylic Trifluoromethanesulfonylation of Aromatic Allylic Alcohols with Sodium Trifluoromethanesulfinate. Journal of Organic Chemistry 81(3): 1304-1309, 2016

Telluride mediated stereospecific conversion of racemic e allylic alcohols to homochiral z allylic alcohols transposition of primary and secondary allylic alcohols via glycidol derivatives. Tetrahedron Letters 31(39): 5603-5606, 1990

Asymmetric hydroformylation of allylic alcohols catalyzed by Rh(I)-(R,S)-BINAPHOS. Tetrahedron Letters 38(26): 4611-4614, 1997

Highly regioselective and diastereoselective directed hydroformylation of allylic ethers: a new approach to propionate aldol synthesis. Journal of the American Chemical Society 123(46): 11514-5, 2001

One-Pot Synthesis of Allylic Sulfones, Ketosulfones, and Triflyl Allylic Alcohols from Domino Reactions of Allylic Alcohols with Sulfinic Acid under Metal-Free Conditions. Chemistry 21(32): 11359-11368, 2015

From olefins to alcohols: efficient and regioselective ruthenium-catalyzed domino hydroformylation/reduction sequence. Angewandte Chemie 52(10): 2949-2953, 2013

FeCl(3).6H(2)O catalyzed disproportionation of allylic alcohols and selective allylic reduction of allylic alcohols and their derivatives with benzyl alcohol. Journal of Organic Chemistry 74(9): 3299-3304, 2009

Directed regio- and stereoselective hydroformylation of mono- and 1,3-disubstituted allylic alcohols: a catalytic approach to the anti-aldol-retron. Chemical Communications: 114-115, 2004

Improved synthesis of isocarbacyclin using regioselective alkylation of allylic alcohols. Tetrahedron Letters 27(52): 6353-6356, 1986

Syntheses of isocarbacyclin by highly regioselective alkylation of allylic alcohols. Tetrahedron 46(19): 6689-6704, 1990

Highly Regioselective Palladium-Catalyzed Carboxylation of Allylic Alcohols with CO2. Chemistry 21(46): 16391-4, 2015

Regioselective reductive coupling of alkynes and aldehydes leading to allylic alcohols. Organic Letters 5(5): 653-655, 2003

Highly efficient and regioselective allylation with allylic alcohols catalyzed by [Mo(3)S(4)Pd(eta(3)-allyl)] clusters. Organic Letters 12(12): 2726-2729, 2010

Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols. Angewandte Chemie 47(10): 1928-1931, 2008

Ruthenium(IV) complexes featuring P,O-chelating ligands: regioselective substitution directly from allylic alcohols. Angewandte Chemie 49(15): 2782-2785, 2010