TRIS(TRIMETHYLSILYL)[H-2]SILANE-TRIETHYLBORANE SYSTEM PRODUCING THE HIGHLY DIASTEREOSELECTIVE DEUTERATION (GREATER-THAN-99 1) OF 2'-BROMO-2'-DEOXYRIBONUCLEOSIDES AND 2'-O-PHENOXYTHIOCARBONYLRIBONUCLEOSIDES AT 0-DEGREES-C/

Authors
KAWASHIMA E UCHIDA S MIYAHARA M ISHIDO Y
Citation
E. Kawashima et al., TRIS(TRIMETHYLSILYL)[H-2]SILANE-TRIETHYLBORANE SYSTEM PRODUCING THE HIGHLY DIASTEREOSELECTIVE DEUTERATION (GREATER-THAN-99 1) OF 2'-BROMO-2'-DEOXYRIBONUCLEOSIDES AND 2'-O-PHENOXYTHIOCARBONYLRIBONUCLEOSIDES AT 0-DEGREES-C/, Tetrahedron letters, 38(42), 1997, pp. 7369-7372
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
42
Year of publication
1997
Pages
7369 - 7372
Database
ISI
SICI code
0040-4039(1997)38:42<7369:TSPTH>2.0.ZU;2-I
Abstract
Reductive protylation and deuteration reactions using (Me3Si)(3)SiH- a nd (Me3Si)(3)(SiH)-H-2-Et3B systems were investigated in view of the d ifferences in bond energy and bond length between the Si-H of (Me3Si)( 3)SiH and the Sn-H of Bu3SnH. Higher diastereoselectivity was obtained in comparison with the reactions using the Bu3SnH - and (Bu3SnH)-H-2- Et3B systems; the (Me3Si)(3)SiH system gave remarkable diastereoselect ivity of 98.7% at 0 degrees C, whereas the other system required tempe ratures below -70 degrees C. (C) 1997 Elsevier Science Ltd.