"Hidden Gems" in Chemistry Letters

19 downloads 406 Views 1MB Size Report
Apr 17, 2010 - OTf. RMgBr. Li2MnCl4 cat. R1. R. +. "Hidden Gems" in Chemistry Letters .... The Tishchenko Reaction: A Cl
"Hidden Gems" in Chemistry Letters

Baran Group Meeting 04/17/2010

Chemistry Letters (1972-2010):

Jun Shi Cl

5. Chem. Lett., 1976, 47

• founded in 1972 • published by The Chemical Society of Japan monthly • first Editor-in-Chief: Teruaki Mukaiyama (633 papers)* • Tamejiro Hiyama: current editor-in-chief since 2003 • 39 volums, 461 issues, 22,143 papers • covers all areas of chemistry • highligh reviews since 2004 • 1.504-impact factor in 2008

Cl

O

tBuOK PhNCO

Br

N H proposed mechanism in this paper:

O

-50°C O

78%

N

O

N Ar

O N Ph

NHAr

6. Chem. Lett., 1977, 471 1. Chem. Lett. 1972, 373/1972, 401 NH2

HS-CH2-CO2Et

O

MeOH

N H

CO,Se, Et3N, R.T.

Et2N NEt2 CO, Se, heat 2. Chem. Lett., 1973, 91 first example of phenylation of nitro-olefin H

Pd(OAc)2

Ph

H

Ph

CN Cl CCOOH 3

Me

CN

NNHTs R

H

NO2

NaOH

N N

NNHTs

PhN2Cl Ar

4. Chem. Lett., 1975, 1333 NH2 Bu3Sn

N NPh

Ph

THF, Et3N reflux

Ar

Ph

NaCO2CF3

Me

DMF, 170°C

9. Chem. Lett. 1977, 569 CO2Me O MeOH

NPh

N

Me Cl

isoamyl nitrite tBuCO2H 60°C

CN CN Cl

Ph Me F F O

O MeOH:AcOH OH 5:1 hν



O

O

10. Chem. Lett., 1980, 825

CH2

CH2 Me

then ClCO2Et

8. Chem. Lett., 2005, 1440, 34(10)

70%

Benzene Ph NO2 reflux 3. Chem. Lett., 1973, 1071 synthesis of 2,5-disubstituted tetrazole H

CO2Et

7. Chem. Lett., 1977, 553

Et2NH

Ph

" S-CH-CO Et " 2

OMe

O

THF

O

2 eq LDA

Me

65%

OH

4-C6H4-Cl

MeHN O

ArCH2NH2

*No Prof. Mukaiyama's chemsitry in Chem. Lett. is included here. Please see Yoshi's GM on Mukaiyama instead FIY.

N

air

O

cat. ArCHO

1

Baran Group Meeting 04/17/2010

"Hidden Gems" in Chemistry Letters

11. Chem. Lett., 1982, 1933 NC

CN

MeS

H2 N

LDA, 60%

17. Chem. Lett. 1987, 1145 O FCl2CCO2Me

CN

N

R1

NEt2

NC

S

NEt2

Me

O NHCOPh

S

Me

Me

SnBu3

+

Me

SnBu3

Pd(OAc)2

R

EtO2C

Ph

R1

14. Chem. Lett., 1987, 809 CONHPh PhS 15. Chem. Lett., 1987, 859

CONHPh PhS

E+

Tol. reflux

84.3%

21. Chem. Lett., 1988, 589

NHBz

DBU thenBzCl RMgBr

OTf 3 eq BuLi

CO2Et

CO2Et Me Me SPh "Selenium Polonovski Reaction" CO2Et

PhSeOTf

O-

20 Chem. Lett., 1987, 1575

tBuOOH

PhS

R2

Me N+

+

R1

Rh2(OAc)4

N2

SPh

19. Chem. Lett., 1987, 1575

13. Chem. Lett., 1987, 5 R

Me

Ph N

PPA 120°C

Zn(cat)-CuCl

CO2Me

18. Chem. Lett., 1987, 1569

NEt2 12.Chem. Lett., 1985, 291 O

R2

F

Jun Shi

Li2MnCl4 cat.

R1 R

"synthesis of diamond by CO and H2"

E

RhCl(CO)(PMe3)2

R

R CO, hν

16. Chem. Lett., 1987, 899 CO2Me N

tBu

tBu

N CO2Me

TsOH Bezene, reflux

tBu

N CO2Me

tBu

2

Baran Group Meeting 04/17/2010

"Hidden Gems" in Chemistry Letters

22. Chem. Lett., 1990, 1125 OH Ar

27. Chem. Lett., 1997, 55

O

TsNCl2 R

R

Ar

MeCN, 35°C

23. Chem. Lett., 1992, 1161 "Transhydroxylation" Ac

P(nBu)3-CCl4

N

R

NC

CN R2OH

NC

H HO R

O R

NC OMe

CN R2OH

O R

SiMe2Ph O Me

Me

Me

OEt

Ph

25. Chem. Lett., 1995, 679

O

R R = alkyl, SiR3

Me

Ph

Me

OMe OMe

R

Ru(H)2(CO)(PPh3)3 R' cat. R

OMe

CoCl2(dpph) cat TMSCH2MgCl Ph (3 eq)

O

26. Chem. Lett., 1995, 681 O

85%

R O

TMS

ether, 20°C, 35h

OMe

Ru(H)2(CO)(PPh3)3 cat. O

CoCl2(dpph) cat TMSCH2MgCl OMe (1.5 eq) Ph

75% SiMe2Ph

40%-99%

OR2

30. Chem. Lett., 2004, 832, 33(7)

Me

EtO2C

SnCl4, R.T.

O

O

99-54%

OR2

CN cat.

O

24. Chem. Lett., 1994, 627

CN

OH

75.6%

N

MeCN, R.T

HO

NC

cat.

O

Cl

Ac

Jun Shi

ether, reflux, 48h

TMS

90%

TMS

31. Chem. Lett., 2005, 194, 34(2)

O

MnO2, CHCl3 reflux

X

R'

O

R, R = alkyl, SiR3 Me O Ru(H)2(CO)(PPh3)3 cat. S

Ph

O

SiMe3 90%

32. Chem. Lett., 2006, 714, 35(7) Cu(hfa)2 cat PhSiH3 + ROH O O

Me

S

SiMe3 Ph

F3C

hfa

PhSiH2OR

CF3 3

"Hidden Gems" in Chemistry Letters

Baran Group Meeting 04/17/2010

37. Chem. Lett., 2008, 1006

33. Chem. Lett., 2007, 1414, 36 (12) OH Ar

O

O2 Ar

Actived Carbon

Ar'

F

F3 C Ar'

O +

Ph

F3 C

N

1) TMSOTf 2) TiCl4,

O

F

F

Cl

O

O

Ar 60-79%

Ph

S+

O

S+

Me

H Ph Si

Tf2O Ar 2,6-di-tBuPyr.

Ph -O

S

ArH S

N

35. Chem. Lett., 2007, 366, 36(3) O

B O

-O

O

Ar

F

[RhCl(cod)2]2

38. Chem. Lett., 2008, 786

34. Chem. Lett., 2007, 36(5), 636 O

Jun Shi

S Ph SMe

Me S

Me

Me

SMe

2,6-di-tBuPyr.

OSi

Tf2O

H

62%

RhCl(PPh3)4 1,2-reduction

40. Chem. Lett., 2009, 38(1), 46

H O

CO2Me

PdCl2, CuCl, CO/O2

Ph Si OSi

H

CO2Me

MeOH

O

75%

RhCl(PPh3)4

41. Chem. Lett., 2009, 38(2), 116 1,4-reduction

36. Chem. Lett. 2007, 52, 36(1) R1

Rh2(OOCCF3)4 cat R2

N

60°C

R1 R2 N H

Ts N

NiCl2dppe CH2(ZnI)2

I

Acetone SiMe3

Ts N Me H2C

Me Si O

Me Me

86%

4

Baran Group Meeting 04/17/2010

"Hidden Gems" in Chemistry Letters Selected Total Syntheses:

42. Chem. Lett. 2009, 38(3), 204 O

1. Chem. Lett., 1990, 1230

R

RNC, Pd(PPh3)4

O

OMe

N CO2Me

CO2Me

Ar 75-96%

Ar Me

43. Chem. Lett. 2009, 38(7), 710 OMe Ni(cod)2/L NaOtBu

R

Jun Shi

MeO

OBn

OBn

O

O O

NR1R2 R

NHR1R2

MeO

OMe

250°C

O

NBn

OBn

OMe

42-89%

OMe OMe

OMe

44. Chem. Lett. 2009, 38(5), 430

OBn H2O2

R

CHO

R

CO2H

Pd(TFA)2

N Bn H

45. Chem. Lett. 2009, 38(5), 484 Het-CO2R Thiamine hydrochloride Het: pyridines, quinolines, quinoxaline

46. Chem. Lett. 2009, 488 O

2. Chem. Lett., 2004, 942 Thiamine hydrochloride

OH

MeO2C

O O

O

H

OTHP

H

X=F

Si Me

H nBuSnH 88%

OH

47. Chem. Lett. 2009, 38(6), 352

Ar

OH

O

EtO2C O

TEMPO NaOCl, KBr

OH

H

H

H THPO

93 ee%, 71%

N2

Me

O

Mn(pic)3

O

O

MeO2C

N Bn H

O

(-)-Mesembrine

Et3N, ROH

Het-CHO

O

H OCO2Et

Pd(PPh3)4 NaH H

Me Ar

Si Me

OH

74-99%

H OHC

CO2H

Sordarincin

H

CO2Et O 5

"Hidden Gems" in Chemistry Letters

Baran Group Meeting 04/17/2010

Selected Reviews: 1. Carotenoid Radicals: Cryptochemistry of Natural Colorants

3. Chem. Lett., 2007, 10 MeO HO

CHO

Jun Shi

MeO

O

MeO

MeO

2. Formation of C–C Bonds via Ruthenium-catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level 2008, 1102

O Me

MeO Br

O

MeO2C

2010,148

O

O

3. Synthesis of Biologically Active Carbazole Alkaloids Using Selective Transition-metal-catalyzed Coupling Reactions 2009, 8 4. Participation of Geminal Bonds in Organic Reactions 820, 2007

DTBMP 200°C MeO

O

O

O

O

200, 2007

6. Alkyl Phosphinites: Versatile Synthetic Intermediates for Dehydration Condensation Reactions 2, 2007 7. Transition Metal-catalyzed Carbochalcogenation of Alkynes 1320, 2006

OMe O

AlCl3 100°C O

CO2Me

824, 2006

Me OH

O Me

OH O

8. Cycloaddition Reactions of Transition Metal-containing Benzopyrylium and Related Zwitterionic Intermediates 1082, 2006 9. The Tishchenko Reaction: A Classic and Practical Tool for Ester Synthesis

74%

O

HO HO2C

OMe

O Me O

HO

5. Catalytic Direct Arylation of Heteroaromatic Compounds

Me

MeO MeO2C

40%

O

CO2H

vinaxathone

10. Ruthenium-catalyzed Reconstructive Synthesis of Functional Organic Molecules via Cleavage of Carbon–Carbon Bonds 1462, 2005 11. Azide Compounds: Nitrogen Sources for Atom-efficient and Ecologically Benign Nitrogen-atom-transfer Reactions 1304, 2005 12. Transition Metal-catalyzed Reactions Using Alkynes as Precursors of Carbene and Vinylidene Complexes 1068, 2005 13. Advances in Iron Catalyzed Cross Coupling Reactions 624, 2005 14. Iminium Alkaloids from Marine Invertebrates: Structure, Biological Activity, and Biogenesis 454, 2005 15. !Sulfoximines: Synthesis and Catalytic Applications 482, 2004 16. Palladium Catalyzed Aerobic Dehydrogenation: From Alcohols to Indoles and Asymmetric Catalysis 362, 2004 6