199442-00-7Relevant academic research and scientific papers
A chemoenzymatic approach to enantiomerically pure amines using dynamic kinetic resolution: application to the synthesis of norsertraline
Thalen, Lisa K.,Zhao, Dongbo,Sortais, Jean-Baptiste,Paetzold, Jens,Hoben, Christine,Baeckvall, Jan-E.
supporting information; experimental part, p. 3403 - 3410 (2009/12/29)
Racemization catalyst 5c and the enzyme Candida antarctica lipase B were combined in a one-pot dynamic kinetic resolution (DKR) of primary amines in which a wide range of amines were transformed to their corresponding amides in up to 95% isolated yield and > 99% ee. The DKR protocol was applicable with either isopropyl acetate or dibenzyl carbonate as the acyl donor. In the latter case, release of the free amine from the carbamate products was carried out under very mild conditions. The racemization of (S)-1-phenylethylamine with several different Ru catalysts was also evaluated. Catalyst 5c, of the Shvo type, was able to selectively racemize amines and was also compatible with the reaction conditions used for DKR. A racemization study of three different amines with varying electronic properties was also performed. Competitive racemization of a 1:1 mixture of the deuterated and non-deuterated amine was carried out with 5c and a primary kinetic isotope effect was observed for all three amines, providing support that the rate-determining step is β-hydride elimination. The chemoenzymatic DKR protocol was applied to the synthesis of norsertraline (16) by using a novel route starting from readily available 1,2,3,4-tetrahydro- 1-naphthy lamine (1o).
SMALL MOLECULE BRADYKININ B1 RECEPTOR ANTAGONISTS
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Page/Page column 77, (2009/04/25)
Disclosed are compounds of formula (I) which are bradykinin B1 receptor (B1R) antagonists. These compounds are useful to treat diseases or relieve adverse symptoms associated with inflammation and pain. The invention encompasses novel compounds and acceptable derivatives thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases involving inflammation and pain.
Six-membered bis(azaphosphorinane), readily available ligand for highly enantioselective asymmetric hydrogenations
Yan, Yongjun,Zhang, Xumu
, p. 1567 - 1569 (2007/10/03)
A new six-membered bis(azaphosphorinane) ligand has been readily prepared starting from an inexpensive chiral epoxide; excellent enantioselectivities (up to over 99% ee) have been achieved in the Rh-catalyzed asymmetric hydrogenations of β-dehydroamino ac
A complementary method to obtain N-acyl enamides using the Heck reaction: Extending the substrate scope for asymmetric hydrogenation
Harrison, Paul,Meek, Graham
, p. 9277 - 9280 (2007/10/03)
A series of N-acyl enamides were prepared using the Heck reaction. Asymmetric hydrogenation provided protected amines in up to 99% ee. A method to prepare N-acyl enamides is reported that is complementary to the existing protocols. Heck reaction of a vari
