266
2
General Synthetic Methods
⊡ Scheme 83
nate 198, which can be further reduced to the phosphine oxide 199 by reaction with sodium
dihydrobis(2-methoxy-ethoxy)aluminate (SMDA) ( > Scheme 83) [130].
5.3.2 Addition to Isolated Double Bond
Dialkyl phosphonates [e. g. HP(O)(OMe) 2 ] can be added to isolated double bonds of the 3nitro derivative 200 to give the 3-nitro-2-phosphonate 201. Also, phenylphosphine can react
with the exocyclic double bond of compound 202 to afford the phosphine 203 in 63% yield
together with a dimeric compound [131]. And compound 203 can be further oxidized to produce the phosphine oxide 204 quantitatively ( > Scheme 84) [132].
⊡ Scheme 84
5.4 Coupling Reaction
A modified Arbuzov reaction has been applied to the coupling of the D-glucal/D-galactal derived vinyl halides 205 and triethyl phosphite at 150 °C in the presence of NiCl 2
2
General Synthetic Methods
⊡ Scheme 83
nate 198, which can be further reduced to the phosphine oxide 199 by reaction with sodium
dihydrobis(2-methoxy-ethoxy)aluminate (SMDA) ( > Scheme 83) [130].
5.3.2 Addition to Isolated Double Bond
Dialkyl phosphonates [e. g. HP(O)(OMe) 2 ] can be added to isolated double bonds of the 3nitro derivative 200 to give the 3-nitro-2-phosphonate 201. Also, phenylphosphine can react
with the exocyclic double bond of compound 202 to afford the phosphine 203 in 63% yield
together with a dimeric compound [131]. And compound 203 can be further oxidized to produce the phosphine oxide 204 quantitatively ( > Scheme 84) [132].
⊡ Scheme 84
5.4 Coupling Reaction
A modified Arbuzov reaction has been applied to the coupling of the D-glucal/D-galactal derived vinyl halides 205 and triethyl phosphite at 150 °C in the presence of NiCl 2