SUBSTRATE-CONTROLLED CROTYLBORATION FROM N-(TERT-BUTOXYCARBONYL)AMINOALDEHYDES

Authors
NIEL G ROUX F MAISONNASSE Y MAUGRAS I PONCET J JOUIN P
Citation
G. Niel et al., SUBSTRATE-CONTROLLED CROTYLBORATION FROM N-(TERT-BUTOXYCARBONYL)AMINOALDEHYDES, Journal of the Chemical Society. Perkin transactions. I, (10), 1994, pp. 1275-1280
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
10
Year of publication
1994
Pages
1275 - 1280
Database
ISI
SICI code
0300-922X(1994):10<1275:SCFN>2.0.ZU;2-G
Abstract
Chiral or achiral (Z)-crotylorganoboron compounds add preferentially a nti to N-(tert-butoxycarbonyl)-amino aldehydes. N-(tert-Butoxycarbonyl )prolinal 3 presents a remarkably high diastereofacial selectivity. Do uble stereodifferentiation, starting from compound 3, allows complete diastereoselective access to the gamma-amino-beta-hydroxy-alpha-methyl acid dolaproine 1 present in the antiproliferative dolastatin 10.