synlett 07/2007 - Thieme Chemistry
synlett 07/2007 - Thieme Chemistry synlett 07/2007 - Thieme Chemistry
Letters VIII Table of Contents 1067 M. Kueny-Stotz G. Isorez S. Chassaing* R. Brouillard 1071 T. K. Pradhan A. Hassner* 1075 M. Kikuchi T. Inagaki H. Nishiyama* 1079 V. Sridharan C. Avendaño J. C. Menéndez* Straightforward Synthesis of Highly Hydroxylated Phloroglucinol-Type 3-Deoxyanthocyanidins HO OH OH R = H, OTBS O R HPF6 AcOH r.t., 24 h HO OH + O R' = H, OH PF 6 – 82–91% (4 examples) Stereoselective Synthesis of Medium-Sized Carbocycles Using Alkoxy Radical Fragmentation as a Key Methodology HO ( )n EtO2C n = 1,2 OAc DIB, I 2, CH 2Cl 2 hν 40–93% OHC ( ) n I OAc CO 2Et Et 3N, CH2Cl2 90–95% OHC ( ) n I CO 2Et Asymmetric Intramolecular Michael Reaction Catalyzed by Proline-Derived Small Anilides H O O R' N H O R N H 1 R (30 mol%) AcOH (30 mol%) CHCl 3–H2O, 30 °C R = H, Me, Et, i Pr H O * O * R' > 90% yield up to 90% de up to 93% ee for trans CAN-Catalyzed Vinylogous Povarov Reactions: The First Three-Component Synthesis of 2-Functionalized Tetrahydroquinolines from Anilines, Cinnamaldehyde and Vinyl Ethers R 1 NH2 OR 2 O H CAN (5–15%) MeCN, r.t. R 1 H N H OR 2 H R'
Table of Contents IX 1083 D. Padmakshan S. A. Bennett G. Otting* C. J. Easton* 1085 S. Hübner H. Neumann D. Michalik S. Klaus D. Strübing A. Spannenberg A. Jacobi von Wangelin M. Beller* 1091 N. Schwarz K. Alex I. A. Sayyed V. Khedkar A. Tillack M. Beller* 1096 M. Shindo* K. Yaji T. Kita K. Shishido Stereocontrolled Synthesis of (S)-g-Fluoroleucine a) protection b) NBS c) AgF d) deprotection F + H3N CO – 2 + H3N CO – 2 Three-Component Reactions of a- and b-Bromo Aldehydes with Amides and Dienophiles – An Easy Way to Versatile 1-Amido-2-Cyclohexenes R 1 O NHR 2 + H O Br 1.0 equiv 2.0 equiv 1.5 equiv R 3 R 4 + O O N toluene 150 °C, 20 min 0.5 mmol/mL MW Titanium-Catalyzed Hydroamination of Propargyl Alcohol Derivatives: Synthesis of 3-Silyloxy-2-methylindoles via Hydrohydrazination TBDMSO N R2 R H2N 1 + 1. Ti(NEt2)4, 2,6-di-tert-butyl- 4-methylphenol, toluene 2. ZnCl2, toluene, 100 °C, 24 h R 1 Br R 3 N R1 O NR 2 R 4 OTBDMS Acid-Catalyzed Nazarov Reaction Controlled by b-Alkoxy Groups O OR acid catalyst (0.001 mol% to 10 mol%) < 3 min r.t. RO O 64–96% yield R 2 Me O O N Letters
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Letters<br />
VIII Table of Contents<br />
1067 M. Kueny-Stotz<br />
G. Isorez<br />
S. Chassaing*<br />
R. Brouillard<br />
1<strong>07</strong>1 T. K. Pradhan<br />
A. Hassner*<br />
1<strong>07</strong>5 M. Kikuchi<br />
T. Inagaki<br />
H. Nishiyama*<br />
1<strong>07</strong>9 V. Sridharan<br />
C. Avendaño<br />
J. C. Menéndez*<br />
Straightforward Synthesis of Highly Hydroxylated Phloroglucinol-Type<br />
3-Deoxyanthocyanidins<br />
HO<br />
OH<br />
OH<br />
R = H, OTBS<br />
O<br />
R<br />
HPF6<br />
AcOH<br />
r.t., 24 h<br />
HO<br />
OH<br />
+<br />
O<br />
R' = H, OH<br />
PF 6 –<br />
82–91% (4 examples)<br />
Stereoselective Synthesis of Medium-Sized Carbocycles Using Alkoxy<br />
Radical Fragmentation as a Key Methodology<br />
HO<br />
( )n<br />
EtO2C n = 1,2<br />
OAc<br />
DIB, I 2, CH 2Cl 2<br />
hν<br />
40–93%<br />
OHC<br />
( ) n<br />
I<br />
OAc<br />
CO 2Et<br />
Et 3N, CH2Cl2<br />
90–95%<br />
OHC<br />
( ) n<br />
I<br />
CO 2Et<br />
Asymmetric Intramolecular Michael Reaction Catalyzed by Proline-Derived<br />
Small Anilides<br />
H<br />
O<br />
O<br />
R'<br />
N<br />
H<br />
O<br />
R<br />
N<br />
H<br />
1 R<br />
(30 mol%)<br />
AcOH (30 mol%)<br />
CHCl 3–H2O, 30 °C<br />
R = H, Me, Et, i Pr<br />
H<br />
O<br />
*<br />
O<br />
*<br />
R'<br />
> 90% yield<br />
up to 90% de<br />
up to 93% ee for trans<br />
CAN-Catalyzed Vinylogous Povarov Reactions: The First Three-Component<br />
Synthesis of 2-Functionalized Tetrahydroquinolines from Anilines,<br />
Cinnamaldehyde and Vinyl Ethers<br />
R 1<br />
NH2<br />
OR 2<br />
O<br />
H<br />
CAN (5–15%)<br />
MeCN, r.t.<br />
R 1<br />
H<br />
N<br />
H<br />
OR 2<br />
H<br />
R'
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