synlett 10/2010 - Thieme Chemistry

Letters
VIII Table of Contents
1493 F. Voss
T. Bach*
1497 P. Wessig*
K. Möllnitz
S. Hübner
1501 N. Purkayastha
G. Haufe*
1505 M. Koley
M. Schnürch
M. D. Mihovilovic*
An Ethynyl-Substituted 1,5,7-Trimethyl-3-azabicyclo[3.3.1]nonan-2-one as a
Versatile Precursor for Chiral Templates and Chiral Photocatalysts
O
H
N
Ar
ArX [Pd 0 ]
Et 3N [CuI]
O
H
N
steric shield and/or photocatalytic unit
ArN 3
Et3N [CuI]
A Short and Efficient Route from myo- to neo-Inositol
HO
HO
OH
OH
OH
OH
9 steps
51%
HO
HO
OH
OH
OH
OH
O
H
N
N
N
Ar
N
An Efficient Access to Conformationally Rigid Amino Acid Analogues with
a Piperidine Skeleton
NH2
N t-Bu CONHMe
H
O
N t-Bu CONHMe
H
t-Bu
i-BuO
N
NH2
O
O
NHMe
Selective and Facile Palladium-Catalyzed Amination of
2-Fluoro-4-iodopyridine in the 4-Position under Microwave Conditions
I
N
F
selective
cross-coupling
+
X
nucleophilic
no
substitution
HN
R2 R 1
2, (2 mol%),
Pd(OAc)
(2 mol%)
BINAP
3, toluene,
K2CO
°C, MW
180
R 2
N
N
R 1
F
(13 examples)
48–84%
R1 aryl, alkyl
=
R 2 = H, alkyl