J. Org. Chem., 1998, 63(15), , DOI: /jo980155d

(1)

J. Org. Chem., 1998, 63(15), 5252-5254, DOI:

10.1021/jo980155d

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(2)

IV-191 CDCL3 5OON HO SS

CEH.0

_Sal4

I

1' a Ir _0~ _7.5 -~ I' _71C. _6.5' T 7 6.0' 5 5' 5.C' 4.5 4.0 PPM 3.'9 3.0 2.5 2.0 1.5 1.0 .5 0.0

O

C

c

01 U k U k Cd

-j

(3)

V1995 American

Lhemical

society

Journal UI Urganic uhemistry

Vb.5

Fage

D2D2 wu

bupplemental

Page

2

ITDAIEfC -Sl--20

41?ef555

TO

E-f-MFNWSSI

TOOBTI

mAU

Area: 36526.2 300 ( 200-u

20

Area: 1 1.3

₈

Area: 16777.6 *0 40 50 60 70

Signal 2: DAD1 C, Sig=208,4 Ref-550,100

Peak RT Type Width Area Height Area

# [min] [min] [mAU*sec] [MAU]

---

I -

I---I---1 55.386 MM 1.392 17022.30273 203.85355 24.2048 2 61.175 MM 1.574 36526.15625 386.83310 51.9383 3 66.053 MM 1.672 16777.64258 167.21823 23.8569 70326.10156

HOQ

OOH

3af4a racemate

(R,R) Whelko then (RR)

Whelko

3% EtOH/Hex, 1 mL/min

757.90491

HOQ

O

S

OH

3a/4a

Signal 2: DADI C, Sig-208,4 Ref-550,100 Peak RT

# (min]

1 54.565 2 61.083 3 66.629

Type Width Area Height Area' [min] [mAU*sec] [mAU] v

-

_{--- I---I--- I}

_---

_{-__}

BP 1.331 88230.79688 919.44458 59.4795 MM 1.674 52820.71484 525.96857 35.6083 MM 1.721 7286.57031 70.55545 4.9121 148338.07813 1515.96863 Totals :

(4)

V-9 MEOH-D4 400MHZ HO,r-\ s OtBu 0b 0. t~uo _{fi SW4b}

,ff

I ____

C

U U A 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4 0 PPM -. 5 3.0 2.5 2.0 1.5 i.0 .5 0.0

f

If

d

(5)

V1995 American Lhemical

society

Journal UI Urganic

uhemistry

Vb.5

Fage

D2D2 wu

bupplemental

Page 4

OtBu

.p-(NO

2

)-C

6

H

4

Inal _{3: DAD1 C, Sig-208,4 Ref-550,100}

3bl4b

racemate

tak RT Type Width Area

I

[min] (min] [mAU*sec]

---1 36.319 MM 2.466 10152.90625 2 42.415 MM 2.932 24681.12695 3 54.130 MM 4.061 11053.45703 Height [mAU]

---68.62478 140.27585 45.36084 Area k 22.1257 53.7862 24.0882

Chiracel

OD

20% IPAHex, 1.2 mLmin

nal

_{3: DADI C, Sig=208,4 Ref-550,10}

0 )k RT (min] 35.948 41.600 51.957

Type Width Area Height [min] [AU*sec] _(mAU]

--- I---I

---MM 2.302 6711.71973 _48.60273 ml 3.060 58810.73828 _320.28876 MM _{4.282 117191.63281} 456.14786

p-(N0

2

)-C

6

H

4 Area 3.6733 32.1873 64.13-94

(6)

V-175 ME0H-04 400MHZ

C

HO * s0

RC(:rOH

_3~

t c

C

U U I " -1II 3.0 2.5 2.0 1.5 1.0 .5 0.0 I I 8.0 7.5 7.0 B.5 6.0 5.5 5.0 4.5 4.0 3.9 PPM

(7)

C-1998 American Chemical Society Journal Ut Organic Chemistry V63 Page 5252 Wu Supplemental Page 6

3c/4c racemate

(R,R) Whelko

20% EtOH/Hex, 1 mL/min

DlATiL I. f 6Pw 4 rTrM I nanu i IMUAln MAU

Signal 3: DAD1 C, Sig=208,4 Ref=550,100

Peak

RT

Type

Width

Area

Height

Area

#

[min]

[mAU*sec]

[mAU

%

1 ---- I---I---I---I

---

I

---1

26.986 BV

0.953 14707.85547

228.47693

22.7680

2

29.343 VV

1.275 34886.23438

401.20688

54.0044

3

34.026 VB

1.582 15004.72754

143.61888

23.2276

64598.81641

773.30267

Analysis Method : C:\HPCHEM\1\METHODS\DAA1.M

(modified after loading)

.ignal 1: DAD1 C, Sig=208,4 Ref=550,100

Peak

RT

Type

Width

Area

Height

#

(min]

[min]

[mAU*seci

[mAUi

I ---- I---I----I---I

--- I

---1

27.819 MM

0.870 352.08032

6.74329

2

30.222 FF

1.035 3704.66479

49.97462

Area

0 --- I

2.9808

31.3646

Totals :

I t

,

.

(8)

TV-188 CDCL3 500 MHZ 3d

f f

1

(t I"

AAlAA~

I" 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 PPM 5]I I. 2 .5 2 V. 5 3 .0 2.5 2.0 1.5 1.0 .5 0.0

lI

C C

C

II

I

A

(9)

MESO C5 CDCL3 400MHZ *1. 4d

C

I

ir

I

3./.

2.5

2.

1.5

1. .5

0.

(10)

V 199 American Lhemical

society

Journal UI Urganic Uhemistry V6.5

Fage

D2D2 wu

bupplemental

Page !) mAU 150- 100-

50-1'0

40 M

n

Signal 1: DADI A, Sig-208,4 Ref-off

Peak RT Type Width Area Height Area

# [min] [min] [mAU*sec] [mAU]

I--I---

I----I

---

I--

---

I---

---

---1 35.889 BV 1.522 10741.79688 89.97542 49.9161 2 41.071 VB 1.686 10777.89746 77.93707 50.0839

Totals : 21519.69531

UAU A, big=ZU,4 --etoTT or btvuL IulaII.v

3dl4d racemate

Silica column

1% EtOH/Hex, I mL/min

167.91249 DAUTUlCg=2084-Tet=5uUof MHW186UU mAU 1000- IQ

Signal 3: DADI C, Sig-208,4 Ref-550,100 Peak RT Type Width Area

# [min] (min] [mAU*secl

---I---

I---

I

---

I---1 30.851 BV 1.473 169090.57813 2 35.231 VV 1.511 60292.35156 Height Area [mAU] v 1600.00452 73.7154 550.84644 26.2846 40

rxn mixture

Silica column

1% EtOHIHex, I mL/min

Totals : 229382.93750 2150.85107

UAU1 U, bIg=2US,4

Ret-bbU,1UU

of MMIW1b9.U mAU

100 50

01

Signal 3: DAD1 C, Sig-208,4 Ref-550,100

Peak RT Type Width Area # [mini [min] ImAU*sec3

S- --- I -- I---I ---1 31.269 SB 1.206 7085.46387 Height Area [MAU1 1

---I

---83.01353 100.0000

4d

recrystallized

Silica column

1% EtOH/Hex, i mL/min

7085.46387 83.01353

S-9

M

-HO

S

KIr:OH

I.

Totals 0-3'o I

(11)

C

lVV8J

American

k-femical

)ociety Journal uI

urganic Lflemistry V6. bi1age

D2D2

Wu

,uppiementai F-age

1u

HO-a C a 2 a --L,. if L L C L Q C, a

OH

* U t i

%C4d

racemate

Chiracel OD

12% IPNHex, I

mL/min

. a0 b C. D C= 2: C, -I - H * 2CD CIN Cc HI Z: cn i M CO L.CDO a: * E o m ": I 2:*

D.a

H *r4 H~ LJC.N to o U M *r .-IC .. J -blc of

LD

-L 414 HO6. 5-0t OI Ch a: Dr C I ..

I

0 m-Li L :1' k

rxn mixture

Chiracel OD

12% IPA/Hex, I ml/min

UAU1 (., big=2U8,4

KefbU,1UU

₀_{ftUBMH-WbUU4.U}

mAU 40- 20

0

Signal 3: DAD1 C, Sig=208,4 Ref=550,100

HOQ

S

Peak RT Type Width Area Height Area

# [min] [min] [mAUsecl [mAU]

1-.0-3B---B 1 1 --- I ---1 9.603 BB 0.390 1590.52661 60.09615 100.0000 L) U0 W. CDi Cn 44-4 CS) t: N CD a: c'- '.NI>Nv **' L H C.--- 1

3d

After recrystallization

Chiracel OD

12% IPNHex, 1 mL/min

:0

(12)

V-i58 B GDCLS 300MHZ

~2TIPSjP.

8

r

OTIP

5

J-I2.0* 1. 1.15 . 80 7.5 7.0 6.5 6.0 5.5 5.0 45 4.0 3 3:0 ppm 2.0 1.5 1.0 .5

(13)

0.0-V-169 CDCL3 400MIZ

.f

I

N

I

(14)

U1995 American

Lhemical

Society

Journal UI Urganic Uhemistry

Vb.

Fage

D2D2 wu

bupplemental

Page 13

7000

6000

O

s

5000-0

O

racemate

**y-TA column, 120* isothermal**

4000

METHOD

_{NAME: M:GTA.MET}

₃

000-SIGNAL FILE:

M:SIGNAL.BNC

AREA X

RT

AREA

TYPE

WIDTH

ARER%

7-280

137713

PB

.173

i9.73814

8.545 139163

PB

.216

50.261814

2000-("o

7

9 Sig.

1 in

C:\PEAK\EXP0RT2\SIGNAL.D

Pk#

Ret Time

Area

Height

Type

Width

Area

%

---