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Investigation of the influence of ß substituent in aldol reactions involving boron enolates of methylketones

Author(s):
Emilio Carlos de Lucca Júnior
Total Authors: 1
Document type: Master's Dissertation
Institution: Universidade Estadual de Campinas (UNICAMP). Instituto de Química
Defense date:
Examining board members:
Teodoro Saul Kaufman; Cláudio Francisco Tormena
Advisor: Luiz Carlos Dias
Abstract

The aldol reactions involving boron enolates 71 (P = TBS, R = t-Bu), 72 (P = PMB, R = t-Bu) and 96 (P = TPS, R = t-Bu) led to the formation of aldol adducts with moderate to good levels of diastereoselectivity, favouring the 1,5-syn isomer. The aldol reactions involving boron enolates 90 (P = Tr, R = t-Bu), 91 (P = Tr, R = Me) and 97 (P = TPS, R = Me) led to the formation of aldol in a 50:50 mixture. The aldol reactions of boron enolate 131 (P = TBS, R = Ph3C) led to excellent levels of diastereoselectivity, favouring the 1,5-syn adduct. (AU)

FAPESP's process: 08/07457-8 - Study of the beta substituent in aldol reactions of boron enolates generated from methylketones
Grantee:Emílio Carlos de Lucca Júnior
Support type: Scholarships in Brazil - Master