Technology Process of (E)-1-(tri-n-butylstannyl)-3-cyclohexyl-2-propen-1-one
There total 1 articles about (E)-1-(tri-n-butylstannyl)-3-cyclohexyl-2-propen-1-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
1,1'-azodicarbonyl-dipiperidine; lithium diisopropyl amide;
In
tetrahydrofuran;
To soln. of Bu3SnLi (prepered from Bu3SnH and LDA in THF at 0°C for 15 min) and aldehyde in THF at -78°C 1,1'-(azodicarbonyl)dipiperidine was added, mixt. was warmed to 0°C and stirring for 1 h at 0°C;; Mixt. was quenched with satd. aq. NH4Cl, extd. with ether, organic layer was washed with 3% HCl, satd. NaHCO3, dried over MgSO4; column chromy.;;
- Guidance literature:
-
With
lithium aluminium tetrahydride; ethanol; (R)-1,1'-Bi-2-naphthol;
In
tetrahydrofuran; ethanol;
Mixt. of LiAlH4 and EtOH in THF was stirred for 30 min, (R)-(+)-BINAL-H was added over 1 h, mixt. was heated to reflux for 50 min; at -78°C acyl stannane was added over 1 h, mixt. was stirred for 24 h at -78°C;; Mixt. was quenched with MeOH, followed by satd. aq. NH4Cl, aq. phase was treated with 3% HCl, extd. with ether, organic layer was concd. and filtered, filtrate concd. under reduced pressure; an ee .apprx. 90%;;
- Guidance literature:
-
With
lithium aluminium tetrahydride;
In
tetrahydrofuran; diethyl ether;
Soln. of Chirald in ether and LiAlH4 in THF was stirred for 2 min and then cooled to -78°C; stannyl ketone in ether was added over 1 h, mixt. was stirred for 1.5 h at -78°C (inert atm.);; Suspn. was warmed to room temp. and washed with 3% aq. HCl, satd. aq. NaHCO3, and brine; organic layer was dried over MgSO4, concd. and quickly chromd. through silica gel (10% ether-hexane);;
