Abstract
(matrix presented) Yttrium-salen complexes effect transacylation between enolesters and chiral secondary alcohols, resulting in varying degrees of kinetic resolution. Even though the enantioselectivity remains modest (kfast/kslow up to 4.81), these results represent the first demonstration of a conceptually new metal-catalyzed acyl transfer process that results in kinetic resolution. On the basis of the solid-state structure of the catalyst, a novel associative mechanistic pathway is proposed for the reaction.
| Original language | English |
|---|---|
| Pages (from-to) | 1607-1610 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 4 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2002 May 2 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Ligand-Assisted Rate Acceleration in Transacylation by a Yttrium - Salen Complex. Demonstration of a Conceptually New Strategy for Metal-Catalyzed Kinetic Resolution of Alcohols. / Lin, Mei Huey; RajanBabu, T. V.
In: Organic Letters, Vol. 4, No. 9, 02.05.2002, p. 1607-1610.Research output: Contribution to journal › Article
TY - JOUR
T1 - Ligand-Assisted Rate Acceleration in Transacylation by a Yttrium - Salen Complex. Demonstration of a Conceptually New Strategy for Metal-Catalyzed Kinetic Resolution of Alcohols
AU - Lin, Mei Huey
AU - RajanBabu, T. V.
PY - 2002/5/2
Y1 - 2002/5/2
N2 - (matrix presented) Yttrium-salen complexes effect transacylation between enolesters and chiral secondary alcohols, resulting in varying degrees of kinetic resolution. Even though the enantioselectivity remains modest (kfast/kslow up to 4.81), these results represent the first demonstration of a conceptually new metal-catalyzed acyl transfer process that results in kinetic resolution. On the basis of the solid-state structure of the catalyst, a novel associative mechanistic pathway is proposed for the reaction.
AB - (matrix presented) Yttrium-salen complexes effect transacylation between enolesters and chiral secondary alcohols, resulting in varying degrees of kinetic resolution. Even though the enantioselectivity remains modest (kfast/kslow up to 4.81), these results represent the first demonstration of a conceptually new metal-catalyzed acyl transfer process that results in kinetic resolution. On the basis of the solid-state structure of the catalyst, a novel associative mechanistic pathway is proposed for the reaction.
UR - http://www.scopus.com/inward/record.url?scp=0000469464&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0000469464&partnerID=8YFLogxK
U2 - 10.1021/ol025809q
DO - 10.1021/ol025809q
M3 - Article
C2 - 11975640
AN - SCOPUS:0000469464
VL - 4
SP - 1607
EP - 1610
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 9
ER -