Efficient diacetoxylation of alkenes via Pd(II)/Pd(IV) process with peracetic acid and acetic anhydride.
A palladium-catalyzed diacetoxylation of alkenes in the presence of peracetic acid and acetic anhydride was developed to produce diacetates efficiently and diastereoselectively. Due to its mild conditions, this method was suitable for a broad range of substrates encompassing conjugated and nonconjugated olefins.
Park
Chan Pil
CP
Loker Hydrocarbon Research Institutute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA.
Lee
Joo Ho
JH
Yoo
Kyung Soo
KS
Jung
Kyung Woon
KW
D000089:Acetic Anhydrides / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010463:Peracetic Acid / Q000737:chemistry*; D013237:Stereoisomerism
D000089:Acetic Anhydrides; D000475:Alkenes; C031800:acetic anhydride; D010165:Palladium; D010463:Peracetic Acid
J Am Chem Soc. 2006 Feb 8;128(5):1460-1
16448111
J Am Chem Soc. 2004 Mar 3;126(8):2300-1
14982422
J Org Chem. 2006 Jun 9;71(12):4481-9
16749777
Org Lett. 2005 Feb 17;7(4):745-8
15704940
Org Biomol Chem. 2008 Nov 21;6(22):4083-8
18972034
Angew Chem Int Ed Engl. 2007;46(30):5737-40
17600808
J Org Chem. 2007 Mar 2;72(5):1859-62
17274660
J Am Chem Soc. 2008 Mar 12;130(10):2962-4
18281992
J Am Chem Soc. 2009 Mar 25;131(11):3846-7
19292485
J Am Chem Soc. 2007 Mar 21;129(11):3076-7
17298071
Science. 1993 Jan 1;259(5091):64-6
8418495