TY - JOUR
T1 - Highly atom efficient catalytic reactions utilizing water and alcohols as reagents
AU - Hamasaki, Akiyuki
AU - Yamamoto, Eiji
AU - Itoh, Hisashi
AU - Tokunaga, Makoto
N1 - Funding Information:
We are grateful to all co-workers for their contributions to the studies described in this account. This work was partly promoted as a collaborative study with Dr. Masaru Utsunomiya (Mitsubishi Chemical Corporation). Financial support from the Ministry of Education, Culture, Science, Sports and Technology (MEXT) , Japan, Japan Science and Technology Agency (JST) , and the New Energy and Industrial Technology Development Organization (NEDO), Mitsubishi Chemical Corporation are also gratefully acknowledged.
PY - 2011/1/1
Y1 - 2011/1/1
N2 - In this accounts, we describe our recent studies on hydrolysis, alcoholysis, and addition of alcohols to organic molecules. The reactions utilizing water and alcohols as a reagent are one of the most basic and simple reactions. The palladium-catalyzed asymmetric hydrolysis and alcoholysis of vinyl ethers gave valuable axially chiral 1,1′-bi-2-naphthol and 1,1′-bi-2-phenol derivatives and chiral P-chirogenic compounds in optically active form. The reaction is applied for hydrolytic deallylation of N-allyl amide and allyl esters. The later one was achieved by palladium/ruthenium dual catalysts which is the first example of catalytic irreversible ester hydrolysis. Gold complexes also catalyzed vinyl ether alcoholysis and hydroalkoxylation of olefins. In the later reaction, simple unactivated olefins can be used as substrates and gave the product in 92% yield. The copper-DTBM-SEGPHOS complex catalyzed alcoholysis of azlactones which is the first example showing zero-order kinetic resolution.
AB - In this accounts, we describe our recent studies on hydrolysis, alcoholysis, and addition of alcohols to organic molecules. The reactions utilizing water and alcohols as a reagent are one of the most basic and simple reactions. The palladium-catalyzed asymmetric hydrolysis and alcoholysis of vinyl ethers gave valuable axially chiral 1,1′-bi-2-naphthol and 1,1′-bi-2-phenol derivatives and chiral P-chirogenic compounds in optically active form. The reaction is applied for hydrolytic deallylation of N-allyl amide and allyl esters. The later one was achieved by palladium/ruthenium dual catalysts which is the first example of catalytic irreversible ester hydrolysis. Gold complexes also catalyzed vinyl ether alcoholysis and hydroalkoxylation of olefins. In the later reaction, simple unactivated olefins can be used as substrates and gave the product in 92% yield. The copper-DTBM-SEGPHOS complex catalyzed alcoholysis of azlactones which is the first example showing zero-order kinetic resolution.
UR - http://www.scopus.com/inward/record.url?scp=78649838773&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=78649838773&partnerID=8YFLogxK
U2 - 10.1016/j.jorganchem.2010.08.053
DO - 10.1016/j.jorganchem.2010.08.053
M3 - Article
AN - SCOPUS:78649838773
VL - 696
SP - 202
EP - 210
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
IS - 1
ER -