3. Stereochemistry. Predict the stereochemistry of the major product formed for each of the following reactions. Give an explanation for your choice. а. ÇHO SiMe3 A ОРМВ MgBr2 • Et20 95% (20:1)

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3. Stereochemistry. Predict the stereochemistry of the major product formed for
each of the following reactions. Give an explanation for your choice.
а.
ÇHO
SiMe3
A
`OPMB
MgBr2 • Et20
95% (20:1)
b.
a. MegAI, Cp2ZrCl2 (cat.)
CICH2CH2CI
B
b.
70%
Br, ZnCl2 (1 eq)
Pd(0) (cat.)
с.
1. CBr4, Ph3P, Zn
2а. п-BuLi (2.1 eq), hexane, THF
2b. H20 workup
CHO
3.
56%
BH, THE
4.
Pd(PPH3)4 (cat.)
NaOEt, toluene, 80 °C
Br
d.
Me
2. TSOH• H20
(1.2 ec)
TBSO.
1а. Ме2CuLi, Elyо
D2 (bicyclic)
94%
D1
1b. NC-CO2ME, HMPA 91%
1c. aq NH,CI workup
toluene, reflux
Transcribed Image Text:3. Stereochemistry. Predict the stereochemistry of the major product formed for each of the following reactions. Give an explanation for your choice. а. ÇHO SiMe3 A `OPMB MgBr2 • Et20 95% (20:1) b. a. MegAI, Cp2ZrCl2 (cat.) CICH2CH2CI B b. 70% Br, ZnCl2 (1 eq) Pd(0) (cat.) с. 1. CBr4, Ph3P, Zn 2а. п-BuLi (2.1 eq), hexane, THF 2b. H20 workup CHO 3. 56% BH, THE 4. Pd(PPH3)4 (cat.) NaOEt, toluene, 80 °C Br d. Me 2. TSOH• H20 (1.2 ec) TBSO. 1а. Ме2CuLi, Elyо D2 (bicyclic) 94% D1 1b. NC-CO2ME, HMPA 91% 1c. aq NH,CI workup toluene, reflux
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