Remote stereocontrol in acyclic systems. Hydride addition to 1,5- and 1,6-hydroxy ketones mediated by metal chelation

Authors
Lawson, EC Zhang, HC Maryanoff, BE
Citation
Ec. Lawson et al., Remote stereocontrol in acyclic systems. Hydride addition to 1,5- and 1,6-hydroxy ketones mediated by metal chelation, TETRAHEDR L, 40(4), 1999, pp. 593-596
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
4
Year of publication
1999
Pages
593 - 596
Database
ISI
SICI code
0040-4039(19990122)40:4<593:RSIASH>2.0.ZU;2-0
Abstract
Acyclic 1,6-hydroxy amino ketones can be reduced to either the anti or syn diols with high 1,6 diastereoselectivity by sequential treatment with a Lew is acid and a borohydride reagent, with the direction of stereocontrol depe nding on the Lewis acid complexant used. For example, with 1a anti:syn rati os of >100:1 [Ti(OiPr)(4)/K-Selectride] and 1:7 [Al(OEt)(3)/K-Selectride] w ere realized. 1,5-Hydroxy amino ketone 4a was reduced with high syn 1,5 dia stereoselectivity [anti:syn = 1:18 with Al(OEt)(3)/K-Selectride]. (C) 1999 Elsevier Science Ltd. All rights reserved.