synlett 07/2007 - Thieme Chemistry
synlett 07/2007 - Thieme Chemistry synlett 07/2007 - Thieme Chemistry
Letters Clusters XII Table of Contents 1127 J. González Marrero L. San Andrés* J. Gutiérrez Luis 1130 T. Harada* C. Kitano K. Mizunashi 1135 Y. K. Kang M. J. Cho S. M. Kim D. Y. Kim* 1139 K.-i. Moriya Y. Hamashima M. Sodeoka* Oxidative C-Ring Opening of Abietane Diterpenes with Ammonium Cerium(IV) Nitrate MeO O H MeO O H O O OMe OMe O CAN MeCN–H2O (2:1) CAN MeCN–H 2O (2:1) O O H H COOMe O COOMe O O OH COOMe Iodine-Atom-Transfer-Type Carbocyclization of 2-(2-Propynyloxy)ethyl Iodides Involving a Lithium Alkylidene Carbenoid Intermediate R1 R2 O R 3 H I Bu I Bu Li THF, 40 °C (1.1 equiv) (0.4 equiv) Asymmetric Electrophilic Fluorination of a-Cyanoalkylphosphonates Catalyzed by Chiral Palladium Complexes O (EtO) 2P CN Ar (PhSO2) 2NF (R)-xylyl-BINAP-Pd (II) EtOH, r.t. O (EtO)2P * CN 2,6-di-tert-butyl-4-methylpyridine Ar F Pd(II)-Catalyzed Asymmetric Fluorination of a-Aryl-a-cyanophosphonates with the Aid of 2,6-Lutidine (EtO) 2P F O CN Ar + SO2Ph N SO2Ph * P P Pd(II) 2,6-lutidine (1 equiv) EtOH, –20 °C 5 mol% in Pd R 3 O (EtO)2P O R 2 ∗ Ar F ~ 98% yield ~78% ee R 1 CN O I I
Table of Contents XIII 1143 J. Ramírez D. P. Huber A. Togni* 1148 A. Hidaka B. Zagipa H. Nagura T. Fuchigami* 1153 N. Shibata* H. Yasui S. Nakamura T. Toru* 1158 G. K. S. Prakash* P. J. Linares-Palomino K. Glinton S. Chacko G. Rasul T. Mathew G. A. Olah* Asymmetric Electrophilic Fluorination of a-Nitro Esters O 2N R 1. base O O 2. Selectfluor O2N O O ® , cinchona alkaloid R F R = Me, i R Pr, Ph, Bn 2 R1 R O N 3 1 2 cinchona alkaloid CD: R1 = H, R2 = H, R3 = vinyl QN: R1 = H, R2 = OMe, R3 = vinyl HQCB: R1 = p-ClBz, R2 = OMe, R3 MeCN–H2O or THF, MeCN up to 91% yield up to 40% ee AcCD: R = Et 1 = Ac, R2 = H, R3 = vinyl AcQN: R1 = Ac, R2 = OMe, R3 = vinyl Regioselective Anodic Fluorination of a-(Arylthio)benzylphosphonate Esters, a-(Arylthio)methylphosphonate Esters and Their Analogues Y ArS P(O)(OEt)2 Y = H, Ar – 2e – , – H + , F – Y F DME or MeNO 2 ArS P(O)(OEt) 2 DNA-Mediated Enantioselective Carbon–Fluorine Bond Formation Friedel–Crafts Alkylations of Arenes with Mono- and Bis(trifluoromethyl)oxiranes in Superacid Medium: Facile Synthesis of a-(Trifluoromethyl)- and a,a-Bis(Trifluoromethyl)-b-Arylethanols R 2 R 1 + R 1 = H, Me, Et, n-Pr R 2 = H, Me O X CF3SO3H Y CH 2Cl 2, 0 °C to r.t. R 1 R 2 70–95% yield OH X Y X = CF3, Y = H, CF3 Clusters
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Letters<br />
Clusters<br />
XII Table of Contents<br />
1127 J. González Marrero<br />
L. San Andrés*<br />
J. Gutiérrez Luis<br />
1130 T. Harada*<br />
C. Kitano<br />
K. Mizunashi<br />
1135 Y. K. Kang<br />
M. J. Cho<br />
S. M. Kim<br />
D. Y. Kim*<br />
1139 K.-i. Moriya<br />
Y. Hamashima<br />
M. Sodeoka*<br />
Oxidative C-Ring Opening of Abietane Diterpenes with Ammonium<br />
Cerium(IV) Nitrate<br />
MeO<br />
O<br />
H<br />
MeO<br />
O<br />
H<br />
O<br />
O<br />
OMe<br />
OMe<br />
O<br />
CAN<br />
MeCN–H2O (2:1)<br />
CAN<br />
MeCN–H 2O (2:1)<br />
O<br />
O<br />
H<br />
H<br />
COOMe<br />
O<br />
COOMe<br />
O<br />
O<br />
OH<br />
COOMe<br />
Iodine-Atom-Transfer-Type Carbocyclization of 2-(2-Propynyloxy)ethyl<br />
Iodides Involving a Lithium Alkylidene Carbenoid Intermediate<br />
R1 R2 O<br />
R 3<br />
H<br />
I<br />
Bu I<br />
Bu Li<br />
THF, 40 °C<br />
(1.1 equiv)<br />
(0.4 equiv)<br />
Asymmetric Electrophilic Fluorination of a-Cyanoalkylphosphonates<br />
Catalyzed by Chiral Palladium Complexes<br />
O<br />
(EtO) 2P CN<br />
Ar<br />
(PhSO2) 2NF<br />
(R)-xylyl-BINAP-Pd (II)<br />
EtOH, r.t.<br />
O<br />
(EtO)2P<br />
*<br />
CN<br />
2,6-di-tert-butyl-4-methylpyridine<br />
Ar F<br />
Pd(II)-Catalyzed Asymmetric Fluorination of a-Aryl-a-cyanophosphonates<br />
with the Aid of 2,6-Lutidine<br />
(EtO) 2P<br />
F<br />
O<br />
CN<br />
Ar<br />
+<br />
SO2Ph N<br />
SO2Ph *<br />
P<br />
P<br />
Pd(II)<br />
2,6-lutidine (1 equiv)<br />
EtOH, –20 °C<br />
5 mol% in Pd<br />
R 3<br />
O<br />
(EtO)2P<br />
O<br />
R 2<br />
∗<br />
Ar F<br />
~ 98% yield<br />
~78% ee<br />
R 1<br />
CN<br />
O<br />
I<br />
I
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