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123.202 Lecture 9 - alkenes
1.
LECTURE NINE alkenes III
©skycaptaintwo@flickr
2.
PREVIOUSLY...
i. BH3 ii. H2O2/ NaOH H OH hydroboration (and hydration)
3.
addition of bromine
Br Br Br Br
4.
Br
Br Br Br stereochemistry racemic mixture of enantiomers Br Br Br Br a meso compound
5.
mechanism
step 1 Br Br :Br H H bromonium ion
6.
mechanism
step 2 Br Br SN2 H Br H H H Br anti attack
7.
but...
Br H H Br Br SN2 Br H H Br H H Br attacks either end
8.
mirror
plane Br Br H H H H Br Br enantiomers Br H H Br H Br Br H (S,S) (R,R)
9.
mechanism
step 1 Br Br :Br H H bromonium ion
10.
mechanism
step 2 Br Br SN2 H Br H Br H H anti attack
11.
but...
Br H Br Br H SN2 Br H Br H H H Br attacks either end
12.
Br
H Br H H Br Br H meso Br Br Br Br H H H H (R,S) (S,R)
13.
meso
mirror plane Br Br H H
14.
©Heidi & Matt@flickr
15.
the
not mechanism Br Br Br H mixture Br Br of all stereoisomers H H
16.
from alkenes: diol formation
epoxides O mCPBA H H O mCPBA O H O H H O stereospecific Cl mCPBA addition
17.
©Oberazzi@flickr
18.
concerted mechanism
R R O O H O H O O O
19.
diol formation
H O H H3O O O H H H H H normally anti addition SN2 HO HO H H H H O H OH H
20.
but...
H H O HO O H H H can give SN1 mixture H HO OH HO O H H H
21.
cation stability
22.
O
O H H OH H H OH H H O base-mediated HO exclusively an H ti addition H OH
23.
O
S HO N O O OH O epothilone A example
24.
S
HO N O O OH O epothilone C CF3 example O O 85% (5:1) O S HO N O O OH O epothilone A
25.
from alkenes: diol formation
KMnO4 HO OH KMnO4 H H HO OH KMnO4 H H stereospecific addition
26.
from alkenes: diol formation
KMnO4 HO OH KMnO4 H H meso HO OH KMnO4 H H stereospecific addition
27.
from alkenes: diol formation
KMnO4 HO OH KMnO4 H H meso HO OH KMnO4 H H stereospecific addition
28.
from alkenes: diol formation
KMnO4 HO OH KMnO4 H H HO OH KMnO4 H H stereospecific additie n racemat o
29.
©Ninja M.@flickr
30.
concerted mechanism O
O O O Mn Mn O O O O H H syn addition stereospecific
31.
mechanism
O O Mn H2O HO OH O O MnO2 H H H H hydrolysis in situ
32.
H
CO2H OH O HN O OMe H OH O OH dynemicin A ©A Hermida@flickr
33.
example
OH N OsO4(cat.), N NMO OH 98% OTBS OTBS OTBS OTBS
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