Publication

Highly Stereoselective Aminohydroxylations of Exo-2-Cyano-7-Oxabicyclo[2.2.1]Hept-5-En-2-Yl Acetate

Pierre Vogel
1991
Journal Articles

Abstract

Protected forms of exo-5-amino-exo-6-hydroxy-7-oxabicyclo [2.2.1]heptan-2-one and of exo-5-amino-endo-6-hydroxy-7-oxabicyclo[2.2.1]heptan-2-one can be obtained readily and with high stereoselectivity from exo-2-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl acetate (+/-)-(7). The processes involve acid promoted rearrangements of N-carbonyl aziridines 10 [(1RS,2SR,4RS,5RS, 6SR)-6-cyano-8-oxa-3-azatricyclo[3.2.10(2,4)]oct-6-yl acetate derivatives] derived from (+/-)-7.

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Pierre Vogel
1991
Journal Articles

Abstract

Official source

Related concepts (9)

Acetic acid

Acetic acid əˈsiːtᵻk, systematically named ethanoic acid ˌɛθəˈnoʊᵻk, is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements. Acetic acid is the second simplest carboxylic acid (after formic acid). It is an important chemical reagent and industrial chemical, used primarily in the production of cellulose acetate for photographic film, polyvinyl acetate for wood glue, and synthetic fibres and fabrics.

Amine

In chemistry, amines (əˈmi:n,_ˈæmi:n, ˈeɪmiːn) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline.

Stereoselectivity

In chemistry, stereoselectivity is the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non-stereospecific creation of a new stereocenter or during a non-stereospecific transformation of a pre-existing one. The selectivity arises from differences in steric and electronic effects in the mechanistic pathways leading to the different products. Stereoselectivity can vary in degree but it can never be total since the activation energy difference between the two pathways is finite: both products are at least possible and merely differ in amount.