CARBON-CARBON BOND FORMING REACTIONS
27
I.A.7.a.la-13 Denmark, S.E. and Griedel, B.D., JOC, 59, 5136; see
also: Denmark, S.E. and Chen, C.-T., TL, 35, 4327.
S^
1) PhCHO, -60°C
ft
ft
11
,THF,H 2 0
M e O ^ V ^ I
*RO
?
2)HF,THF,H 2 0 MeO^ ^
^Ph
^
^
M e
97% ee
Me
I.A.7.a.la-14 Carreira, E.M. et al., JACS, 116, 8837; see also: idem,
TL, 35, 4323; Floriani, C. et al., OM, 13, 2131; see also: Regellin, M. and
Weinberger, H., AG(E), 33, 444.
0
T M S
l)cat.
?
H
R'CHO +
= /
3R
- / — 4 —
72-98%, 88-97% ee
^ R
2)Bu 4 NF
R l ^ ^
^
O R
cat. = a chiral Ti species
similarly with other Ti catalysts
I.A.7.a.la-15 Hanaoka, M. et al., SL, 165; see also: idem, TL, 35,
6899; Braun, M. et al., CB, 127, 1959.
,CHO
Me
ί ΐ Ί ^
^ ^
.OTMS
l)BF 3 ^OEt 2
M e O ^ y ^ ^ T M S
L
2
>
raAF
/
S
l Bu
3ì CAN
Cr(CO) 3
MeO
69%,anti : syn = 15.7 : 1
Cp2ZrCl2 also used for anti selective aldols
27
I.A.7.a.la-13 Denmark, S.E. and Griedel, B.D., JOC, 59, 5136; see
also: Denmark, S.E. and Chen, C.-T., TL, 35, 4327.
S^
1) PhCHO, -60°C
ft
ft
11
,THF,H 2 0
M e O ^ V ^ I
*RO
?
2)HF,THF,H 2 0 MeO^ ^
^Ph
^
^
M e
97% ee
Me
I.A.7.a.la-14 Carreira, E.M. et al., JACS, 116, 8837; see also: idem,
TL, 35, 4323; Floriani, C. et al., OM, 13, 2131; see also: Regellin, M. and
Weinberger, H., AG(E), 33, 444.
0
T M S
l)cat.
?
H
R'CHO +
= /
3R
- / — 4 —
72-98%, 88-97% ee
^ R
2)Bu 4 NF
R l ^ ^
^
O R
cat. = a chiral Ti species
similarly with other Ti catalysts
I.A.7.a.la-15 Hanaoka, M. et al., SL, 165; see also: idem, TL, 35,
6899; Braun, M. et al., CB, 127, 1959.
,CHO
Me
ί ΐ Ί ^
^ ^
.OTMS
l)BF 3 ^OEt 2
M e O ^ y ^ ^ T M S
L
2
>
raAF
/
S
l Bu
3ì CAN
Cr(CO) 3
MeO
69%,anti : syn = 15.7 : 1
Cp2ZrCl2 also used for anti selective aldols