Abstract
Asymmetric hydrogenation of keto-acids was accomplished by catalytic amounts of BINAP-ruthenium complexes to afford the corresponding δ-lactones in high yields. The optical purity of the synthesised δ-lactones was determined by chiralcel (OD) in the 9–56% range.
References
1.
Siegel S.
, Encyclopedia of Reagents for Organic Synthesis ;
Paquette
L.A.
, Ed.; John Wiley & Sons : Chichester , 1996 ; Vol. 6 , p 4410 .
2.
(a)
Bennett M.A.
and
Matheson T.W.
, In Comprehensive Organometallic Chemistry ;
Wilkinson G.
,
Stone F.G.A.
and
Abel E.W.
, Eds.; Pergamon Press: Oxford, 1982 ; Vol. 4 , p 931
3.
James B.R.
, Homogeneous Hydrogenation; Wiley : New York , 1973
4.
Freifelder M.
, Practical Catalytic Hydrogenation ; Wiley-Interscience : New York , 1971 .
5.
(a) Review:
Chaloner P.A.
,
Esteruelas M.A.
,
Joó F.
and
Oro L.A.
, Homogeneous Hydrogenation ; Kluwer Academic Publishers: Dordrecht, 1994 ; Chapter 4, p 119
6.
Halpern J.
,
Harrod J.F.
and
James B.R.
, J. Am. Chem. Soc. 1966 , 88 , 5150 .
7.
(a)
Tsuji J.
and
Suzuki H.
, Chem Lett. , 1977 , 1085
8.
Sánchez-Delgado
R.A.
and
de Ochoa
O.L.
, J. Mol. Catal. , 1979 , 6 , 303
9.
Sánchez-Delgado
R.A.
,
Andriollo
A.
,
de Ochoa
O.L.
,
Suárez
T.
and
Valencia N.J.
, J. Organomet. Chem. , 1981 , 209 , 77
10.
Grosselin J.M.
,
Mercier C.
,
Allmang G.
and
Grass F.
, Organometallics , 1991 , 10 , 2126 .
11.
Osakada K.
,
Ikariya T.
and
Yoshikawa S.
, J. Organmet. Chem. 1982 , 231 , 79
12.
Sungborn C.
and
Tanaka K.
, Bull. Chem. Soc. Jpn. , 1982 , 55 , 2275
13.
Bonnet M.
,
Geneste P.
and
Rodriguez M.
, J. Org. Chem. , 1980 , 45 , 40 .
14.
(a)
Bianchi M.
,
Mench G.
,
Francalanci F.
,
Piacenti F.
,
Matteoli U.
,
Frediani P.
and
Botteghi C.
, J. Organomet. Chem. , 1980 , 188 , 109
15.
Lyons J.E.
, J. Chem. Soc. Chem. Commun. , 1976 , 314;
Hara Y.
and
Wada K.
, Chem. Lett., 1991, 553.
16.
Tuenissen H.T.
and
Elsevier C.J.
, J. Chem. Soc. Chem. Commun. , 1997 , 667.
17.
Ishii Y.
,
Ikariya T.
,
Saburi M.
and
Yoshikawa S.
, Tetrahedron Lett . 1986 , 27, 365.
18.
(a)
Masui M.
and
Shioiri T.
, SynLett 1996 , 49
19.
Evans D.A.
,
Nelson S.G.
,
Gagné M.R.
and
Muci A.R.
, J. Am. Chem. Soc. 1993 , 115 , 9800
20.
Mathre D.
,
Jones T.K.
,
Xavier L.C.
,
Blacklock T.J.
,
Reamer R.A.
,
Mohan J.J.
,
Jones E.T.
,
Hoogsteen K.
,
Baum M.W.
and
Grabowski E.J.
, J. Org. Chem. , 1991 , 56 , 751 .
21.
(a)
Ohta T.
,
Miyake T.
,
Seido N.
,
Kumobayashi H.
,
Akutagawa S.
and
Takaya H.
, Tetrahedron Lett. , 1992 , 33 , 635
22.
Ohta T.
,
Miyake T.
and
Takaya H.
, J. Chem. Soc., Chem. Commun. , 1992 , 1725.
23.
Osakada K.
,
Ikariya
T.
Yoshikawa
S.
, J. Organomet. Chem. , 1982 , 231 , 79 .
24.
(a)
Ohloff G.
, Fortschr. Chem. Org. Naturst. 1978 , 35 , 431
25.
Mulzer J.
, In Compr. Org. Funct. Group Transform ;
Katrizky A.R.
,
Meth-Cohn
O.
and
Rees C.W.
Eds.; Elsevier: Oxford, 1995 ; Vol. 5 , 121
26.
Ley S.V.
,
Cox L.R.
and
Meek G.
, Chem. Rev. 1996 , 96 , 423
27.
Collins I.
, J. Chem. Soc., Perkins Trans . 1 1998 , 1869
28.
Mcrae K.J.
and
Rizzacasa M.A.
, J. Org. Chem. 1997 , 62 , 1196
29.
Urabe H.
,
Matsuka T.
and
Sato F.
, Tetrahedron Lett. , 1992 , 33 , 4183 .
30.
(a)
Ikariya T.
,
Ishii Y.
,
Kawano H.
,
Arai T.
,
Saburi M.
,
Yoshikawa S.
,
Akutagawa S.
, J. Chem. Soc., Chem. Commun. , 1985 , 922
31.
Noyori R.
,
Ohta M.
,
Hsiao Y.
,
Kitamura M.
, J. Am. Chem. Soc. , 1986 , 108 , 7117
32.
Noyori R.
,
Ohkuma T.
,
Kitamura M.
, J. Am. Chem. Soc. , 1987 , 109 , 5856
33.
Ohta T.
,
Takaya H.
and
Noyori R.
, Inorg. Chem. , 1988 , 27 , 566 .
34.Neither [RuH2{(S)-BINAP}2] nor [RuCl2{(S)-BINAP}] can provide catalysis on 1a at 100°C, the conversion of substrate was below 15% when the reaction temperature was 120°C.
35.
Naota T.
,
Takaya H.
and
Murahashi S.I.
, Chem. Rev. , 1998 , 98 , 2599 .
