10.1021/jo060592p.s001
Marisa Mena
Marisa
Mena
Josep Bonjoch
Josep
Bonjoch
Domingo Gomez Pardo
Domingo Gomez
Pardo
Janine Cossy
Janine
Cossy
Ring Expansion of Functionalized Octahydroindoles to Enantiopure
<i>cis</i>-Decahydroquinolines<sup>†</sup>
American Chemical Society
2006
ci
ring Expansion
reaction conditions
MsCl
THF
analogue
AgOAc
ethylene
isomer
acetal
Endo
ring enlargement
rt
Et 3N
TFAA
Enantiopure
exo derivatives
benzyl
Functionalized Octahydroindoles
endo
enantiopure
hydroxyethyl
entry
2006-08-04 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Ring_Expansion_of_Functionalized_Octahydroindoles_to_Enantiopure_i_cis_i_Decahydroquinolines_sup_sup_/3066568
A new synthetic entry to enantiopure <i>cis</i>-decahydroquinolines is reported. Endo and exo derivatives of
<i>cis</i>-1-benzyl-2-(hydroxymethyl)octahydroindol-6-one ethylene acetal undergo ring enlargement upon
treatment with TFAA and then Et<sub>3</sub>N (thermodynamic conditions) to give enantiopure 1-benzyl-3-hydroxydecahydroquinolin-7-one derivatives in 77 and 82% yield, respectively. For 2-(1-hydroxyethyl)
analogues, the best synthetic result is obtained from the (2<i>S</i>,1‘<i>R</i>) endo isomer, which under kinetic reaction
conditions (MsCl, THF, −20 °C, then AgOAc at rt ) gives the expanded product in 54% yield.