APPENDIX 3 - California Institute of Technology · Appendix 3 – Spectra Related to Chapter 3 220...

Appendix 3 – Spectra Related to Chapter 3

APPENDIX 3

Spectra Related to Chapter 3:

Construction of Vicinal Tertiary and All-Carbon Quaternary

Stereocenters via Ir-Catalyzed Regio-, Diastereo-, and Enantioselective

Allylic Alkylation and Applications in Sequential Pd-Catalysis

272


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Figu

re A

3.1

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 100a

.

OPh CO

2Me

100a

273


��

Figure A3.2 Infrared spectrum (thin film/NaCl) of compound 100a.

Figure A3.3 13C NMR (125 MHz, CDCl3) of compound 100a.

274


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�

�

��

��

��

Figu

re A

3.4

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 100b

.

OCO

2Me

100b

OMe

275


��

Figure A3.6 Infrared spectrum (thin film/NaCl) of compound 100b.

Figure A3.6 13C NMR (125 MHz, CDCl3) of compound 100b.

276


��

�

�

��

��

��

Figu

re A

3.7

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 100c

.

OCO

2Me

100c

Br

277


��

Figure A3.8 Infrared spectrum (thin film/NaCl) of compound 100c.

Figure A3.9 13C NMR (125 MHz, CDCl3) of compound 100c.

278


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�

�

��

��

��

Figu

re A

3.10

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 100d

.

OCO

2Me

100d

CF3

279


��

��

��

Figure A3.11 Infrared spectrum (thin film/NaCl) of compound 100d.

Figure A3.12 13C NMR (125 MHz, CDCl3) of compound 100d.

280


��

�

�

��

��

��

Figu

re A

3.13

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 100e

.

OCO

2Me

100e

N

281


��

Figure A3.14 Infrared spectrum (thin film/NaCl) of compound 100e.

Figure A3.15 13C NMR (125 MHz, CDCl3) of compound 100e.

282


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�

�

��

��

��

Figu

re A

3.16

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 100f

.

OCO

2Me

100f

S

283


��

Figure A3.17 Infrared spectrum (thin film/NaCl) of compound 100f.

Figure A3.18 13C NMR (125 MHz, CDCl3) of compound 100f.

284


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�

�

��

��

��

Figu

re A

3.19

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 100g

.

OCO

2Me

100g

O

285


020406080100120140160180200ppm

Figure A3.20 Infrared spectrum (thin film/NaCl) of compound 100g.

Figure A3.21 13C NMR (125 MHz, CDCl3) of compound 100g.

286


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�

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��

��

Figu

re A

3.22

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 100h

.

OCO

2Me

100h

287


��

Figure A3.23 Infrared spectrum (thin film/NaCl) of compound 100h.

Figure A3.24 13C NMR (125 MHz, CDCl3) of compound 100h.

288


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�

�

��

��

��

Figu

re A

3.25

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 100i

.

OPh CO

2Et

100i

289


��

Figure A3.26 Infrared spectrum (thin film/NaCl) of compound 100i.

Figure A3.27 13C NMR (125 MHz, CDCl3) of compound 100i.

290


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�

�

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��

��

Figu

re A

3.28

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 103a

.

CO2Et

103a

OPh

291


��

Figure A3.29 Infrared spectrum (thin film/NaCl) of compound 103a.

Figure A3.30 13C NMR (125 MHz, CDCl3) of compound 103a.

292


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��

��

Figu

re A

3.31

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 103b

.

OPh CO

2Et

103b

293


��



294


-2

-1

01

23

45

67

89

10

11

12

13

14

ppm

Figu

re A

3.34

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 103c

.

OPh CO

2CH2CH2TMS

103c

295


020406080100120140160180200220ppm



296


��

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��

Figu

re A

3.7

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 103d

.

OPh CO

2Me

103d

i-BuO

297


��

Figure A3.38 Infrared spectrum (thin film/NaCl) of compound 103d.

Figure A3.39 13C NMR (125 MHz, CDCl3) of compound 103d.

298


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��

Figu

re A

3.40

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 103e

.

OOPh CO

2Me

103e

299


��

Figure A3.41 Infrared spectrum (thin film/NaCl) of compound 103e.

Figure A3.42 13C NMR (125 MHz, CDCl3) of compound 103e.

300


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�

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��

Figu

re A

3.43

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 103f

.

N BnOPh CO

2Me

103f

301


��

Figure A3.44 Infrared spectrum (thin film/NaCl) of compound 103f.

Figure A3.44 13C NMR (125 MHz, CDCl3) of compound 103f.

302


-2

-1

01

23

45

67

89

10

11

12

13

14

ppm

Figu

re A

3.46

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 10

6a a

nd 1

07a.

PhO

106a

PhO

107a

major

minor

303


020406080100120140160180200220ppm

Figure A3.47 Infrared spectrum (thin film/NaCl) of compound 106a and 107a.

Figure A3.48 13C NMR (125 MHz, CDCl3) of compound 106a and 107a.

304


-2

-1

01

23

45

67

89

10

11

12

13

14

ppm

Figu

re A

3.49

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 106b

.

PhO

106b

Ph

305


020406080100120140160180200220ppm



306


12

34

56

78

910

ppm

Figu

re A

3.52

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 106c

.

PhO

106c

Me

307


020406080100120140160180200220ppm



308


-1.0

-0.5

0.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

f2 (

ppm

)

-1

0 1 2 3 4 5 6 7 8

f1 (ppm)

NO

ESY01

CM

RV

-245-all2

Figu

re A

3.55

1 H N

OSE

Y N

MR

(600

MH

z, C

DC

l 3) o

f com

poun

d 108.

O

108

Ph

309


020406080100120140160180200220ppm

Figure A3.56 Infrared spectrum (thin film/NaCl) of compound 108.

Figure A3.57 13C NMR (125 MHz, CDCl3) of compound 108.

310


-1

01

23

45

67

89

10

11

12

13

14

ppm

Figu

re A

3.58

1 H N

MR

(500

MH

z, C

6D6)

of c

ompo

und L14.

PN

O

CF3

Ph

PhF 3C

L14

311


020406080100120140160180200220ppm

126128130132134136138140142144146148ppm

Figure A3.59 Infrared spectrum (thin film/NaCl) of compound L14.

Figure A3.60 13C NMR (125 MHz, C6D6) of compound L14.

312


-180

-160

-140

-120

-100

-80

-60

-40

-20

020

ppm

Fig

ure

A3.6

1 19

F N

MR

(282

MH

z, C

6D6)

of c

ompo

und L14.

PN

O

CF3

Ph

PhF 3C

L14

313


-22

-20

-18

-16

-14

-12

-10

-8

-6

-4

ppm

Figu

re A

3.62

31P

NM

R (1

21 M

Hz,

C6D

6) o

f com

poun

d L14.

PN

O

CF3

Ph

PhF 3C

L14

314


-1

01

23

45

67

89

10

11

12

13

14

ppm

Figu

re A

3.63

1 H N

MR

(500

MH

z, C

6D6)

of c

ompo

und L15.

PN

O

CF3

F 3C

CF3

L15

315


020406080100120140160180200220ppm

Figure A3.64 Infrared spectrum (thin film/NaCl) of compound L15.

Figure A3.65 13C NMR (125 MHz, C6D6) of compound L15.

316


-200

-180

-160

-140

-120

-100

-80

-60

-40

-20

020

ppm

Figu

re A

3.66

19F

NM

R (2

82 M

Hz,

C6D

6) o

f com

poun

d L8

.

PN

O

CF3

F 3C

CF3

L15

317


-40

-20

020

40

60

80

100

120

140

160

180

200

ppm

Figu

re A

3.67

31 P

NM

R (1

21 M

Hz,

C6D

6) o

f com

poun

d L15.

PN

O

CF3

F 3C

CF3

L15

318

APPENDIX 3 - California Institute of Technology · Appendix 3 – Spectra Related to Chapter 3 220...

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Transcript of APPENDIX 3 - California Institute of Technology · Appendix 3 – Spectra Related to Chapter 3 220...