STEREOSELECTIVE HYDROXYALKYLATION OF TITANATED ALLYL SULFOXIMINES AT THE ALPHA-POSITION AS WELL AS THE GAMMA-POSITION THROUGH VARIATION OF THE TITANATION REAGENT

Authors
HAINZ R GAIS HJ RAABE G
Citation
R. Hainz et al., STEREOSELECTIVE HYDROXYALKYLATION OF TITANATED ALLYL SULFOXIMINES AT THE ALPHA-POSITION AS WELL AS THE GAMMA-POSITION THROUGH VARIATION OF THE TITANATION REAGENT, Tetrahedron : asymmetry, 7(9), 1996, pp. 2505-2508
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
9
Year of publication
1996
Pages
2505 - 2508
Database
ISI
SICI code
0957-4166(1996)7:9<2505:SHOTAS>2.0.ZU;2-C
Abstract
Titanation of the lithioallyl sulfoximines E-2 and 2-2 with ClTi(NEt(2 ))(3) gives allyltitanium species which react with aldehydes highly re gio- and diastereoselectively at the alpha-position to form the syn-al pha-hydroxalkyl allyl sulfoximines E-3 and Z-3, respectively. With ClT i(OiPr)(3) as the titanation reagent anti-gamma-hydroxyalkyl vinyl sul foximines are obtained instead with equally high selectivities. NMR sp ectroscopic evidence points to the formation of the monoallyltitanium sulfoximine E-l upon reaction of E-2 withClTi(NEt(2))(3). Copyright (C ) 1996 Elsevier Science Ltd