Diastereoselective synthesis of 2-phenylselenenyl-1,3-anti-diols and 2-phenylselenenyl-1,3-anti-azido-alcohols via hydroxy and azido-selenenylation reactions.
A method to synthesize 2-phenylselenenyl-1,3-anti-diols and 2-phenyl- selenenyl-1,3-anti-azidoalcohols via hydroxy- or azido-selenenylation of trans-allylic alcohols is reported. Moreover, the first example of hydroxyl-selenenylation of an allylic azide is presented. Yields ranging from moderate to good and diastereomeric ratios up to 95:5 are achieved.
Riela
Serena
S
Dipartimento di Chimica Organica E. Paternò, Università di Palermo, Viale delle Scienze, Parcod'Orleans II, Pad. 17, 90128, Palermo, Italy.
Aprile
Carmela
C
Gruttadauria
Michelangelo
M
Meo
Paolo Lo
PL
Noto
Renato
R
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D006900:Hydroxylation; D008954:Models, Biological; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D064586:Selenic Acid; D018036:Selenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000438:Alcohols; D016566:Organoselenium Compounds; D020005:Propanols; D018036:Selenium Compounds; C006463:allyl alcohol; D064586:Selenic Acid