A novel asymmetric route to 2-amino-1,2,3,4-tetrahydronaphthalenes
β Scribed by Michael C.J Harris; Mark Jackson; Ian C Lennon; James A Ramsden; Helen Samuel
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 173 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
A novel asymmetric route to 2-amino-1,2,3,4-tetrahydronaphthalenes has been demonstrated starting from phthalimidovinylglycinol (PVG). Functionalisation of PVG via Heck reaction, olefin hydrogenation and cyclisation provides the title products.
π SIMILAR VOLUMES
2R,3R)-Dihydroxy-tetrahydronaphthalene, prepared via an efficient chemoenzymatic procedure from naphthalene, has been successfully tested, as a chiral auxiliary in diastereoselective conjugate additions of lithium dialkylcuprates to 0t,13-unsaturated esters and in stereoselective alkylations of 13-k
The synthesis and resolution of cis-1-amino-2-hydroxy-1,2,3,4tetrahydronaphthalene 5 by a simple and straightforward methodology has been achieved. The homochiral aminoalcohol has been used in the catalytic reduction of ketones by means of BH 3 .SMe2 affording secondary alcohols in high enantiomeric