Addition of chiral allyltrichlorostannanes to achiral methylketones and isatins

Author(s)

Valeria de Assis Vasconcelos

• Document type: Master's Dissertation
• Press: Campinas, SP.
• Institution: Universidade Estadual de Campinas (UNICAMP). Instituto de Química
• Defense date: 2009-07-31

Examining board members

Luiz Carlos Dias; Angelo da Cunha Pinto; Antonio Claudio Herrera Braga

• Advisor: Luiz Carlos Dias

Abstract

The preparation of homoallylic alcohols through the addition of an organometallic allylic reagent to aldehydes is one of the most important processes in organic synthesis. The objective of this work was to investigate the reactions of chiral allyltrichlorostannanes (1, 2 and 3) with achiral methyl ketones and isatins leading to homoallylic alcohols containing a quaternary stereogenic center. The coupling reaction of achiral methyl ketones with chiral allyltrichlorostannanes (R)-1, (S)-2 and (R)-3 (prepared in situ from the allylsilanes) gave the corresponding homoallylic alcohols with low to moderate levels of diastereoselectivity. The coupling reaction of N-alkyl isatins with chiral allyltrichlorostannanes (R)-1, (S)-2 and (R)-3 gave the corresponding homoallylic alcohols with low to high levels of diastereoselectivity, in good yields. (AU)