Biomaterial Database

One-pot stereoselective synthesis of 1,2-amino alcohol derivatives. 2011

Alicia Boto, and Iván Romero-Estudillo

Instituto de Productos Naturales y Agrobiología CSIC, Avda. Astrofísico Fco. Sánchez 3, 38206-La Laguna, Tenerife, Spain. alicia@ipna.csic.es

Common β-hydroxy amino acids (such as threonine) can be readily transformed into 1,2-amino alcohols with excellent stereoselectivity. This one-pot decarboxylation-alkylation process allows the replacement of the carboxyl group by alkyl, allyl, or aryl groups, generally in high yields. A variation of the process (decarboxylation-Diels-Alder) allows the formation of bi- and polycyclic systems, which are useful precursors of alkaloid cores or iminosugars.

UI	MeSH Term	Description	Entries
D000478	Alkylation	The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group.	Alkylations
D000605	Amino Alcohols	Compounds possessing both a hydroxyl (-OH) and an amino group (-NH2).	Alcohols, Amino
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular