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Fukuyama Group - Group Meeting Problems 10/06/2012: J. Rodriguez Et Al., Org. Lett., 12, 4212 (2010)

The document summarizes four recent research articles. Article 1 describes a method to synthesize a cyclic boron compound using a borylation reaction. Article 2 details a two-step synthesis of a cyclic ether using BF3-mediated cyclization and TfOH-promoted rearrangement. Article 3 involves a rhodium-catalyzed cycloaddition to form a cyclic nitrile oxide. Article 4 reports a gold-catalyzed cycloisomerization to form a spirocyclic product using microwave irradiation.

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28 views3 pages

Fukuyama Group - Group Meeting Problems 10/06/2012: J. Rodriguez Et Al., Org. Lett., 12, 4212 (2010)

The document summarizes four recent research articles. Article 1 describes a method to synthesize a cyclic boron compound using a borylation reaction. Article 2 details a two-step synthesis of a cyclic ether using BF3-mediated cyclization and TfOH-promoted rearrangement. Article 3 involves a rhodium-catalyzed cycloaddition to form a cyclic nitrile oxide. Article 4 reports a gold-catalyzed cycloisomerization to form a spirocyclic product using microwave irradiation.

Uploaded by

Anonymous rhUNqC1s0
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Fukuyama Group - Group Meeting Problems

10/06/2012
1
N2

O Ph

microwave

+ Ph

+ BnNH2

toluene, 140 C

NBn
O

73%

J. Rodriguez et al., Org. Lett., 12, 4212 (2010)

2
1) PhI(OAc)2 (1.2 eq.)
HFIP, 0 C

OMe

HO
O Si O

OH

MeO

H O
OMe

2) TBAF, THF, rt
40% (2 steps)
S. Canesi et al., J. Org. Chem., 77, 7588 (2012)

3
p-TolSO2Na

O
TBS

DMF, rt
80%

PhCH2Br

TBAF

NaHMDS, THF
80 to 60 C

THF
80 to 70 C

93%

86%

Ph

K. Takeda et al., Org. Lett., 6, 4849 (2004)

4
MeO OTES

PhCH2N3, BF3OEt2

Rh2(OAc)4

78 C to rt
CH2Cl2

CH2Cl2, 0 C to rt

O
N
Ph

90%

47%

J. Aube et al., Org. Lett., 2, 1657 (2000)

Fukuyama Group - Group Meeting Problems


10/13/2012
(pin)BB(pin) (3 eq)
Cu(OAc)2 (2 mol%)
P(t-Bu)3 (7 mol%)

1
MeO

toluene, 80 C

OMe

62%

C28H52O8B4

1H

NMR (CDCl)3
1.12 (s, 24 H)
1.26 (s, 24 H)
1.85 (s, 4 H)

toluene, 100 C

Ph
OH

OH

PhCHO (3 eq)

Ph

Ph

86%

H. Yoshida et al., Angew. Chem. Int. Ed., 51, 235 (2012)


T. Hiyama et al., Chem. Asian. J., 2, 1142 (2007)

1) MeO
Li

Et

t-BuO

OMe

THF, 78 C
52%
2) toluene, reflux;
Ag2O, K2CO3, rt
92%
3) TFA, toluene, 0 C
quant.

H2O2, Na2CO3
dioxane-H2O
60 C;
HCl aq.
H2SO3 aq.
0 C;

NaOH
CuSO4

The intermediate
contains
5-membered ring. H2O, 70C

O
HO

OMe

Me
O

72%

OMe

H. W. Moore et al., J. Org. Chem., 60, 461 (1995)

3
Me
N
Ph

COCF3
O

Me3S I, n-BuLi
THF, 20 C to rt;
AcOH, 80 C

MeS
Ph

70% (2 steps)

CF3
N
Me

M. Kawase et al., Tetrahedron Lett., 53, 2782 (2012)

4
O

1) MeO
Cl
Et3N, CH2Cl2, rt
2) p-TsOHH2O
THF-H2O, reflux

3) NaIO4, NaHCO3 aq
CH2Cl2, rt
53% (3 steps)

Br

Monocyclic
Compound

1) Me
In (powder)
THF-NH4Cl aq, 0 C
77%
2) MsCl, Et3N
hydroquinone
toluene
190 C (sealed tube)
47%

OMs
Me
H H

MeO
N

B. Alcaide et al., Eur. J. Org. Chem., 98 (2005)

Fukuyama Group - Group Meeting Problems


10/31/2012
1

SPh2BF4

N3

KOH

TiCl4

DMSO
0 C to rt

CH2Cl2
78 C to rt
78% (2 steps)
S. Baskaran et al., Chem. Commun., 48, 5778 (2012)

2
Me

1) BF3OEt2
CDCl3, rt
quant.

O
Ph
Ph

O
O

2) TfOH (20 eq.)


CDCl3, 30 C
98%

Me

Ph

Me

Me

T. Oshima et al., Eur. J. Org. Chem., 3917 (2012)

3
TMS

O
N2

Rh2(esp)2 (0.5 mol%)

TBAF

CH2Cl2, rt

THF, 45 C

71%

63%

O
O

J. A. May et al., J. Am. Chem. Soc., 134, 17877 (2012)

4
Ph
OMe
(OC)5Cr

Ph

n-BuLi, THF, 78 C;
TMSOTf;
, CH3CN
73%

spiro
compound

[(JohnPhos)Au(CH3CN)][SbF6]
(5 mol%)

Ph

DCE, 100 C, W
Ph
41%

J. Barluenga et al., Angew. Chem., 124, 10523 (2012)

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