Vol. 69, 2004 Ho-Kee Yim and Henry N. C. Wong*. Diastereoselective Addition Reactions of Furyl Sulfonylimine Using Chiral Boronates as Auxiliary: Application to the Enantioselective Synthesis of 2,3-Disubstituted Furyl Sulfonylamides.
Page 2895, Table 3. Table 3 should have appeared as shown below. The description in the Supporting Information has been changed accordingly.
Page 2893, left column. The text should read, “It was found that diastereomers 9a-d were more polar than diastereomers 8a-d”, instead of “It was found that the R diastereomers 8a-d were more polar than S diastereomers 9a-d”. Page 2893, Table 1. Table 1 should have appeared as shown below. The description in the Supporting Information has been changed accordingly.
TABLE 3. Suzuki Coupling Reactions of 8 and 9
TABLE 1. Addition Reactions of Various Nucleophiles to 7a
starting
conditiona
R
product
yield (%)
8b 8c 8d 9b 9c 9d
A B B A B B
t-Bu Me3SiCH2 CH2dC(SiMe3) t-Bu Me3SiCH2 CH2dC(SiMe3)
12a 12b 12c 13a 13b 13c
62 88 82 64 90 82
a A ) Ba(OH) , PhMe/MeOH (1:1), reflux, 2 h. B ) 2 M K PO , 2 3 4 DME/H2O (4:1), reflux, 2 h.
Page 2895, Figure 5. Figure 5 should have appeared as shown below. The description in the Supporting Information has been changed accordingly.
entry
nucleophile
1 2 3 4 5 6 7
n-BuLi n-BuLi n-BuLi t-BuLi Me3SiCH2MgCl Me3SiCH2MgCl Me3SiCH2MgCl
8
Me3SiCH2MgCl
9 10 11 12 13
Me3SiCH2MgCl Me3SiCH2MgCl CH2dC(SiMe3)MgBr CH2dC(SiMe3)MgBr CH2dC(SiMe3)MgBr
14
CH2dC(SiMe3)MgBr
conditions (solvent, yieldb T (°C)) products (%) THF, -78 DME, -60 PhMe, -78 THF, -78 THF, -40 DME, -30 THF/Et2O 1:4 THF/Et2O 1:8 DCM, -40 PhH, -40 THF, -40 DME, -30 THF/Et2O 1:4 THF/Et2O 1:8
dec (%)
8a 8a 8a 8b 8c 8c 8c
9a 9a 9a 9b 9c 9c 9c
45 58 64 35 94 81 88
33 (9a) 33 (9a) 33 (9a) 33 (9b) 20 (9c) 83 (9c) 80 (9c)
8c
9c
85
86 (9c)
8c 8c 8d 8d 8d
9c 9c 9d 9d 9d
82 78 90 75 80
25 (9c) 56 (9c) 25 (9d) 74 (9d) 78 (9d)
8d
9d
76
80 (9d)
a All reactions were carried out by adding nucleophiles (4 equiv) to furyl sulfonylimine 7. b Total isolated yield of 8 and 9. c Determined by 1H NMR analysis of crude mixture. The major diastereomer is indicated in the parentheses.
5158
J. Org. Chem. 2004, 69, 5158
FIGURE 5. Oxidative rearrangement of 13b and 16.
JO040003K 10.1021/jo040003k Published on Web 06/24/2004
