Abstract
A simple procedure for reductive amination of aliphatic carbonyls, giving direct access to free primary amines using low–valent titanium (LVT) reagent has been reported.
References
1.
Whitesell
J.K.
, In Comprehensive Organic Synthesis , eds
Trost
B.M.
, and
Fleming
I.
, Pergamon , Oxford , 1991 , Vol 8 , and references cited therein.
2.
(a)
Tararov
V.I.
,
Kadyrov
R.
,
Riermeier
T.H.
, and
Borner
A.
, Chem Commun. , 2000, 1867 , and references therein
3.
Johnson
H.E.
, and
Crossby
D.G.
, J. Org. Chem. , 1962 , 27 , 2205
4.
Emerson
W. S.
, Org. React. , 1948 , 4 , 174 .
5.
(a)
Hutchins
R.O.
, and
Natale
N.R.
, Org. Prep. Proc. Int. , 1979 , 11 , 201
6.
Lane
C.F.
, Synthesis , 1975 , 135
7.
Borch
R.F.
,
Bernstein
M.D.
, and
Durst
H.D.
, J. Am. Chem. Soc. , 1971 , 93 , 2897
8.
Yoon
N.M.
,
Kim
E.G.
,
Son
H.S.
, and
Choi
J.
, Synth. Commun. , 1993 , 23 , 1595
9.
Brussee
J.
,
van Benthem
R.A.T.M
,
Kruse
C.G.
, and
van der Gen
A.
, Tetrahedron Asymmetry , 1990 , 1 , 163
10.
Bhattacharyya
S.
,
Chatterjee
A.
, and
Duttachowdhury
S.K.
, J. Chem. Soc., Perkin Trans. 1 , 1994 , 1
11.
Bhattacharyya
S.
,
Chatterjee
A.
, and
Williamson
J.S.
, Synth. Commun. , 1997 , 23 , 4265
12.
Abdel-Magid
A.F.
,
Carson
K.G.
,
Harris
B.D.
,
Maryanof
C.A.
, and
Shah
R.D.
, J. Org. Chem. , 1996 , 61 , 3849 , and references therein
13.
Gribble
G.W.
, and
Ferguson
D.C.
, J. Chem. Soc., Chem. Commun. , 1975 , 535
14.
Gribble
G.W.
,
Jasinski
J.M.
,
Pellicone
J.T.
, and
Panetta
J.A.
, Synthesis , 1978 , 766
15.
Ranu
B.C.
,
Majee
A.
, and
Sarkar
A.
, J. Org. Chem. , 1998 , 63 , 370 .
16.
Chen
B.C.
,
Sundeen
J.E.
,
Guo
P
,
Bednarz
M.S.
, and
Zhao
R.
, Tetrahedron Lett. , 2001 , 42 , 1245 .
17.
Apodaca
R.
, and
Xiao
W.
, Org. Lett. , 2001 , 3, 1745 .
18.
Moormann
A. E.
, Synth. Commun. , 1993 , 23 , 789 .
19.
For some selected references on modulation of LVT reagents, see: (a)
Rele
S.
,
Talukdar
S.
,
Banerji
A.
, and
Chattopadhyay
S.
, J. Org. Chem. , 2001 , 66 , 2990
20.
Rele
S.
,
Chattopadhyay
S.
, and
Nayak
S.K.
, Tetrahedron Lett. , 2001 , 42 (in press)
21.
Talukdar
S.
,
Nayak
S.K.
, and
Banerji
A.
, J. Org. Chem. , 1998 , 63 , 4925
22.
Talukdar
S.
, and
Banerji
A.
, J. Org. Chem. , 1998 , 63 , 3468
23.
Banerji
A.
, and
Nayak
S.K.
, J. Chem. Soc., Chem Commun. , 1991 , 1443
24.
Balu
N.
,
Nayak
S.K.
, and
Banerji
A.
, J. Am. Chem. Soc. , 1996 , 25 , 5932 .
25.
Other selected references, see: (a)
Rele
S.
,
Talukdar
S.
, and
Banerji
A.
, Tetrahedron Lett. , 1999 , 40 , 767
26.
Talukdar
S.
, and
Banerji
A.
, Synth. Commun. , 1995 , 25 , 813
27.
Talukdar
S.
, and
Banerji
A.
, Synth. Commun. , 1996 , 26 , 1051
28.
Talukdar
S.
,
Nayak
S.K.
, and
Banerji
A.
, Synth. Commun. , 1998 , 28 , 2325 .
29.
For some excellent reviews see: (a)
McMurry
J.E.
, Chem. Rev. , 1989 , 89 , 1513
30.
Fürstner
A.
, Active Metals – Preparation, Characterization, Applications, Weinheim, VCH, 1996 , pp. 85 –131
31.
McMurry
J.E.
,
Fleming
M.P.
,
Kees
K.L.
, and
Krepski
L.R.
, J. Org. Chem. , 1978 , 43 , 3255
32.
Lenoir
D.
, Synthesis, 1989 , 883
33.
Furstner
A.
, and
Bogdanovic
B.
, Angew. Chem. Int. Ed. Engl. , 1996 , 35 , 2442
34.
Hegedus
L.S.
, Comprehensive Organometallic Chemistry II , Pergamon , Oxford , 1995 , Vol. 12 , pp. 1071
35.
Dams
R.
,
Malinowski
M.
,
Westdrop
I.
, and
Geise
H.Y.
, J. Org. Chem. , 1982 , 47 , 248 .
