Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: stereoselective synthesis of a d-ribo-phytosphingosine derivative

Authors :: Jeon, Jongho
Shin, Moonyong
Yoo, Jae Won
Oh, Joon Seok
Bae, Jae Gwang
Jung, Seung Hwan
Kim, Young Gyu
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Feb2007, Vol. 48 Issue 7, p1105-1108. 4p.
Publication Year :: 2007
Abstract: Abstract: Protection of 1,2-dialkyl substituted (Z)-allylic amines with an N,N-diBoc group resulted in an opposite stereoselectivity in the OsO4-catalyzed dihydroxylation reactions to that of N-Boc-(Z)-allylic amines. A higher anti selectivity (>10:1) was shown in CH2Cl2. An efficient stereoselective synthesis of a tetraacetyl derivative of d-ribo-phytosphingosine was reported using the N,N-diBoc-controlled dihydroxylation from Garner’s aldehyde. [Copyright &y& Elsevier]

Language :: English
ISSN :: 00404039
Volume :: 48
Issue :: 7
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 23739929
Full Text :: https://doi.org/10.1016/j.tetlet.2006.12.084

Full Text Access

Tools