synlett 10/2010 - Thieme Chemistry

synlett 10/2010 - Thieme Chemistry synlett 10/2010 - Thieme Chemistry

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Letters VI Table of Contents 1459 A. Ghoshal A. R. Sarkar G. Manickam R. S. Kumaran J. Jayashankaran* 1463 S. Paul R. Jana J. K. Ray* 1469 A. Alizadeh* Z. Noaparast H. Sabahnoo N. Zohreh 1473 L. Jean-Gérard F. Macé H. Dentel A. Ngoc Ngo S. Collet* A. Guingant* M. Evain Rhodium-Catalyzed Asymmetric Hydrosilylation of Ketones Employing a New Ligand Embodying the Bis(oxazolinyl)pyridine Moiety H HO O Rh catalyst, Ph 2SiH 2, AgBF 4 THF, 10 °C 94% yield, 98% ee O N (S) R N Rh Cl Cl Cl Rh catalyst Palladium-Catalyzed Intramolecular C–H Activation: A Synthetic Approach towards Polycyclic Aromatic Hydrocarbons Br CHO Br OH An Unprecedented and Concise Method for the Synthesis of 1,3-Thiazino-[3,4a][1,3]benzimidazoles via a Three-Component Reaction R NH 2 NH2 + Ar NCS + H CO2Me CH2Cl 2–toluene reflux, 10 h A New Synthesis of (R)-(–)-Sumanirole (PNU-95666E) Ph N O N O O epoxidation MCPBA Ph N O O N O O steps R HN Ar N N N N O N sumanirole S O (S) NHMe •HCl

Table of Contents VII 1477 A. A. Esmaeili* R. Hosseinabadi A. Habibi 1481 C. Chaulet C. Croix J. Basset M.-D. Pujol M.-C. Viaud-Massuard* 1485 S. Sobhani* S. Rezazadeh 1489 M. Ayaz B. Westermann* An Efficient Synthesis of Highly Functionalized 4H-Pyrano[3,2-d]isoxazoles via Isocyanide-Based Three-Component Reaction R 1 N C: + CO 2R 2 CO2R 2 + Ph N O O MeCN reflux Ph N O CO2R 2 O CO 2R 2 Desulfonylation of Indoles and 7-Azaindoles Using Sodium tert-Butoxide X N R SO2Ph NaOt-Bu dioxane tube sealed 80 °C X N H X = CH, N HClO 4–SiO 2 as a Novel and Recyclable Catalyst for the Phospha-Michael Addition of Phosphorous Nucleophiles to a,b-Unsaturated Malonates R 2 X R1 P(OEt)3 + Y R1 aryl, heteroaryl, alkyl = R2 alkyl, H = = CN, CO2Et, NO2 X = CN, CO2Et, H Y HClO 4–SiO 2 (3 mol%) solvent-free R O P(OEt)2 Enantioenriched Naphthoquinone Mannich Bases by Organocatalyzed Nucleophilic Additions to in situ Formed Imines O O OH 10 mol% cat. α-amidosulfones N H Me2N S N H R 1 R 2 Y X NH R 1 O O OAc R up to 94% yields up to 65% ee NHPG Letters

Letters<br />

VI Table of Contents<br />

1459 A. Ghoshal<br />

A. R. Sarkar<br />

G. Manickam<br />

R. S. Kumaran<br />

J. Jayashankaran*<br />

1463 S. Paul<br />

R. Jana<br />

J. K. Ray*<br />

1469 A. Alizadeh*<br />

Z. Noaparast<br />

H. Sabahnoo<br />

N. Zohreh<br />

1473 L. Jean-Gérard<br />

F. Macé<br />

H. Dentel<br />

A. Ngoc Ngo<br />

S. Collet*<br />

A. Guingant*<br />

M. Evain<br />

Rhodium-Catalyzed Asymmetric Hydrosilylation of Ketones Employing a<br />

New Ligand Embodying the Bis(oxazolinyl)pyridine Moiety<br />

H HO<br />

O<br />

Rh catalyst, Ph 2SiH 2, AgBF 4<br />

THF, <strong>10</strong> °C<br />

94% yield, 98% ee<br />

O<br />

N<br />

(S)<br />

R<br />

N<br />

Rh<br />

Cl Cl<br />

Cl<br />

Rh catalyst<br />

Palladium-Catalyzed Intramolecular C–H Activation: A Synthetic Approach<br />

towards Polycyclic Aromatic Hydrocarbons<br />

Br<br />

CHO<br />

Br<br />

OH<br />

An Unprecedented and Concise Method for the Synthesis of<br />

1,3-Thiazino-[3,4a][1,3]benzimidazoles via a Three-Component Reaction<br />

R<br />

NH 2<br />

NH2<br />

+<br />

Ar NCS<br />

+<br />

H<br />

CO2Me<br />

CH2Cl 2–toluene<br />

reflux, <strong>10</strong> h<br />

A New Synthesis of (R)-(–)-Sumanirole (PNU-95666E)<br />

Ph<br />

N<br />

O N<br />

O<br />

O<br />

epoxidation<br />

MCPBA<br />

Ph<br />

N<br />

O<br />

O N<br />

O<br />

O<br />

steps<br />

R<br />

HN<br />

Ar<br />

N<br />

N<br />

N<br />

N<br />

O<br />

N<br />

sumanirole<br />

S<br />

O<br />

(S)<br />

NHMe<br />

•HCl

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