Organic Letters 2013-03-15

Kinetic resolution of racemic 2-hydroxy-γ-butyrolactones by asymmetric esterification using diphenylacetic acid with pivalic anhydride and a chiral acyl-transfer catalyst.

Kenya Nakata, Kouya Gotoh, Keisuke Ono, Kengo Futami, Isamu Shiina

文献索引：Org. Lett. 15(6) , 1170-3, (2013)

全文：HTML全文

摘要

Various optically active 2-hydroxy-γ-butyrolactone derivatives are produced via the kinetic resolution of racemic 2-hydroxy-γ-butyrolactones with diphenylacetic acid using pivalic anhydride and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst. Importantly, the substrate scope of this novel protocol is fairly broad (12 examples, s-value; up to over 1000). In addition, we succeeded in disclosing the reaction mechanism to afford high enantioselectivity using theoretical calculations and expounded on the substituent effects at the C-3 positions in 2-hydroxylactones.

相关化合物

  • 特戊酸酐

相关文献：

The concept of superactive esters. Could peptide synthesis be improved by inventing superactive esters?

1994-03-01

[Int. J. Pept. Protein Res. 43 , 312, (1994)]

Observation and elimination of N-acetylation of oligonucleotides prepared using fast-deprotecting phosphoramidites and ultra-mild deprotection.

2001-05-07

[Bioorg. Med. Chem. Lett. 11(9) , 1105-1107, (2001)]

New synthetic substrates of mammalian nucleotide excision repair system.

2013-07-01

[Nucleic Acids Res. 41 , e123, (2013)]

Structural Basis for Substrate Specificity in Adenosylcobalamin-dependent Isobutyryl-CoA Mutase and Related Acyl-CoA Mutases.

2015-11-06

[J. Biol. Chem. 290 , 26882-98, (2015)]

Kinetic resolution of the racemic 2-hydroxyalkanoates using the enantioselective mixed-anhydride method with pivalic anhydride and a chiral acyl-transfer catalyst.

2010-01-04

[Chemistry 16(1) , 167-72, (2010)]

更多文献...