1284
M. Hiersemann
PAPER
Table 5 1H NMR Data of b-Hydroxy Esters 3a-r,a 300 MHz, CDCl3
Compound d, J (Hz)
3a
0.90 (t, J = 7.3, 3 H), 1.21 (d, J = 6.5, 3Hmajor), 1.22 (d, J = 6.5, 3Hminor), 1.41 (qt, J1 = J2 = 7.4, 2 H), 2.03 (td, J1 = J2 = 7.4,
2 H), 2.43 (br d, J = 6.5, 1Hmajor), 2.55 (br d, J = 4.9, 1Hminor), 3.74 (d, J = 5.5, 1Hminor), 3.77 (s, 3Hminor), 3.78 (s, 3Hmajor),
3.88-4.21 (m, 4Hmajor, 3Hminor), 5.48-5.61 (m, 1 H), 5.65-5.77 (m, 1H)
1.17-1.24 (m, 3 H), 1.28-1.35 (m, 3 H), 2.36-2.49 and 2.56-2.61 (br m, 1 H), 3.725 and 3.734 and 3.77 (s, 3 H), 3.82-4.10
(m, 3 H), 5.08-5.24 (m, 3 H), 5.58-5.87 (m, 1 H)
3bb
3c
0.90 (t, J = 7.5, 3 H), 0.99 (t, J = 7.5, 3 H), 1.39 (qt, J1 = J2 = 7.4, 2 H), 1.47-1.62 (m, 2 H), 2.03 (dt, J1 = J2 = 7.3, 2 H), 2.31
(br s, 1 H), 3.70-3.84 (m, partially covered, 1 H), 3.78 (s, 3 H), 3.84 (d, J = 4.6, 1Hminor), 3.95 (d, J = 4.9, 1Hmajor), 4.01-
4.11 (m, 1 H), 4.19-4.29 (m, 1 H), 5.48-5.70 (m, 1 H)
3d
3e
3f
0.90 (t, J = 7.5, 3 H), 0.98 (t, J = 7.5, 3Hminor), 0.99 (t, J = 7.5, 3Hmajor), 1.41 (qt, J1 = J2 = 7.4, 1 H), 1.47-1.60 (m, 2 H), 2.03
(td, J1 = J2 = 7.0, 2 H), 2.36 (d, J =7.0, 1 H), 3.77 (s, 3 H), 3.71-3.97 (m, 3 H), 4.11-4.22 (m, 1 H), 5.47-5.60 (m, 1 H),
5.64-5.77 (m, 1 H)
0.898 (t, J = 7.3, 3Hminor), 0.903 (t, J = 7.3, 3Hmajor), 1.22 (d, J = 6.5, 3Hminor), 1.23 (d, J = 6.4, 3Hmajor), 1.42-1.47 (m, 2 H),
2.30 (td, J1 = J2 = 7.4, 2 H), 2.62-2.64 (br m, 1 H), 3.376 (s, 3Hminor), 3.381 (s, 3Hmajor), 3.60-3.63 (m, 2 H), 3.79-3.81 and
3.90-4.78 (m, 6 H), 5.55-5.59 (m, 1 H), 5.66-5.76 (m, 1 H)
0.87 (t, J = 7.4, 3 H), 0.92-0.98 (m, 3 H), 1.37 (qt, J1 = J2 = 7.4, 2 H), 1.46-1.62 (m, 2 H), 2.01 (dt, J1 = J2 = 6.9, 2 H), 2.37
(d, J = 7.3, 1Hminor), 2.45 (d, J = 6.2, 1Hmajor), 3.34 (s, 3Hmajor), 3.35 (s, 3Hminor), 3.59 (ddd, J1 = J2 = J3 = 4.8, 2 H), 3.72-3.80
(m, 1 H), 3.87-3.92 (m, 2 H), 4.09-4.18 (m 1 H), 4.23-4.40 (m, 2 H), 5.46-5.56 (m, 1 H), 5.63-5.72 (m, 1 H)
0.98 (t, J = 7.5, 3Hminor), 1.02 (t, J = 7.3, 3Hmajor), 1.29 (d, J = 6.2, 6 H), 1.45-1.63 (m, 2 H), 1.67 (s, 3 H), 1.76 (s, 3 H), 2.31
(d, J = 6.2, 1Hmajor), 2.37 (d, J = 6.2, 1Hminor), 3.68-3.88 (m, 2H), 3.92-4.03 (m, 1 H), 4.13-4.23 (m, 1 H), 5.13 (sept, J =
6.3, 1 H), 5.30-5.39 (m, 1 H)
3g
3h
3i
1.208 (d, J = 6.5, 3Hmajor), 1.214 (d , J = 6.2, 3Hminor), 1.29 (d, J = 6.5, 6 H), 1.68 (s, 3 H), 1.76 (s, 3H), 2.48 (d, J = 6.8,
1Hmajor), 2.62 (d, J = 4.9, 1Hminor), 3.65 (d, J = 6.2, 1Hminor), 3.84 (d, J = 4.6, 1Hmajor), 3.91-4.24 (m, 3 H), 5.13 (sept, J = 6.3,
1 H), 5.35 (m, 1 H)
0.90 (t, J = 7.3, 3 H), 1.21 (d, J = 6.5, 3Hmajor), 1.22 (d, J = 6.2, 3Hminor), 1.28 (d, J = 6.2, 6 H), 1.41 (qt, J1 = J2 = 7.4, 2 H),
2.03 (dt, J1 = J2 = 7.3, 2 H), 2.38 (d, J = 7.1, 1Hmajor), 2.54 (d, J = 5.2, 1Hminor), 3.67 (d, J = 5.5 1Hminor), 3.86 (d, J = 4.6,
1Hmajor), 3.88-4.22 (m, 3 H), 5.12 (sept, J = 6.3, 1 H), 5.49-5.61 (m, 1 H), 5.64-5.76 (m, 1 H)
0.90 (t, J = 7.3, 3 H), 1.21 (d, J = 6.5, 3Hmajor), 1.22 (d, J = 6.5, 3Hminor), 1.29 (d, J = 6.5, 6 H), 1.39 (qt, J1 = J2 = 7.4, 2 H),
2.04 (td, J1 = J2 = 7.3, 2 H), 2.49-2.55 (br m, 1Hmajor), 2.60-2.65 (br m, 1Hminor), 3.67 (d, J = 5.8, 1Hminor), 3.86 (d, J = 4.6,
1Hmajor), 3.92-4.11 and 4.19-4.30 (m, 3H), 5.13 (sept, J = 6.3, 1H), 5.49-5.70 (m, 1 H)
3j
3k
3l
0.90 (t, J = 7.5, 3 H), 0.98 (t, J = 7.5, 3Hminor), 0.99 (t, J = 7.5, 3Hmajor), 1.28 (d, J = 6.2, 6Hminor), 1.28 (d, J = 6.5, 6Hmajor),
1.41 (qt, J1 = J2 = 7.4, 2 H), 1.47-1.62 (m, 2 H), 2.03 (td, J1 = J2 = 7.0, 2 H), 2.27-2.37 (m, 1 H), 3.69-3.84 and 3.87-3.96
(m, 3 H), 4.11-4.20 (m, 1 H), 5.12 (sept, J = 6.3, 1 H), 5.48-5.60 and 5.64-5.76 (m, 2 H)
1.23 (d, J = 6.5, 3Hmajor), 1.24 (d, J = 6.2, 3Hminor), 1.28 (d, J = 6.2, 3 H), 1.29 (d, J = 6.2, 3 H), 1.77 (s, 3H), 2.40 (br d, J =
6.2, 1Hmajor), 2.54 (br d, J = 5.5, 1Hminor), 3.69 (d, J = 5.5, 1Hminor), 3.82-3.90 (m, 2Hmajor, 1Hminor), 4.03-4.18 (m, 2 H), 4.93
(br s, 1 H), 4.98 (br s, 1 H), 5.13 (sept, J =6.3, 1 H)
3m
3n
3o
3p
0.75-1.01 (m, 9 H), 1.28 (d, J = 7.1, 6 H), 1.35-1.47 (m, 2 H), 1.79-1.93 (m, 1 H), 1.99-2.06 (m, 2 H), 2.20 (d, J = 7.6,
1Hminor), 2.34 (d, J = 4.6, 1Hmajor), 3.49 (m, 1Hminor), 3.61 (m, 1Hmajor), 3.86-3.93 (m, 2 H), 4.09-4.29 (m, 1 H), 5.07-5.19
(m, 1 H), 5.48-5.58 (m, 1 H), 5.65-5.75 (m, 1 H)
0.89 (t, J = 7.3, 3 H), 0.97 (d, J = 6.5, 3Hminor), 1.08 (d, J = 6.2, 3Hmajor), 1.16 (d, J = 6.2, 3Hmajor), 1.17 (d, J = 6.5, 3Hminor),
1.38 (qt, J1 = J2 = 7.4, 2 H), 1.99 (td, J1 = J2 = 7.3, 2 H), 3.09 (br s, 1 H), 3.82-3.97 and 4.02-4.13 (m, 2 H), 3.97 (d, J = 6.5,
1Hminor), 4.07 (d, J = 5.8, 1Hmajor), 4.84-5.03 (m, 2 H), 5.35-5.50 and 5.57-5.69 (m, 2 H), 7.23-7.41 (m, 5 H)
1.23 (d, J = 6.2, 3Hminor), 1.27 (d, J = 6.2, 3Hminor), 1.30 (d, J = 6.2, 6Hmajor), 1.67 (s, 3 H), 1.76 (s, 3 H), 2.30 and 2.40 (br s,
1 H), 2.73-2.83 and 2.86-2.98 (m, 2 H), 3.72 (d, J = 3.9, 1Hminor), 3.86 (d, J = 5.2, 1Hmajor), 3.92-4.03 and 4.06-4.25 (m, 2
H), 5.10 (sept, J = 6.3, 1Hminor), 5.14 (sept, J = 6.3, 1Hmajor), 5.32-5.41 (m, 1 H), 7.19-7.33 (m, 5 H)
0.90 (t, J = 7.3, 3 H), 1.30 (d, J = 6.2, 6 H), 1.33-1.47 (m, 2 H), 1.96-2.07 (m, 2 H), 2.28 (d, J = 5.8, 1Hmajor), 2.37 (d, J =
7.5, 1Hminor), 2.73-2.97 (m, 2 H), 3.72-3.76 and 3.84-3.96 (m, 2 H), 4.06-4.23 (m, 2 H), 5.06-5.19 (m, 1 H), 5.49-5.76
(m, 2 H), 7.18-7.35 (m, 5 H)
3qb
3r
1.22-1.38 (m, 9 H), 2.14-2.44 (br m, 1 H), 2.30-2.36 and 2.39-2.45 and 2.68-3.00 (br m, 1 H), 3.73-3.76 and 3.85-4.15
(m, 3 H), 5.04-5.22 (m, 3 H), 5.59-5.73 and 5.75-5.90 (m, 1 H), 7.16-7.39 (m, 5 H)
1.27 (d, J = 7.1, 3Hminor), 1.30 (d, J = 6.2, 3Hmajor), 1.76 (s, 3Hmajor), 1.81 (s, 3Hminor), 2.26 (br s, 1Hmajor), 2.37 (br s, 1Hminor),
2.75-2.85 and 2.87-3.00 (m, 2 H), 3.77 (d, J = 3.6, 1Hminor), 3.84 (br s, 1Hminor), 3.88 (d, J = 4.9, 1Hmajor), 3.88 (br s, 1Hmajor),
4.07-4.19 (br m, 2 H), 4.92 (br s, 1Hmajor), 4.95 (br s, 1Hminor), 4.97 (br s, 1Hmajor), 5.01 (br s, 1Hminor), 5.14 (sept, J = 6.3,
1H), 7.16-7.34 (m, 5 H)
a Determined from a mixture of 2 diastereomers. Diastereomeric ratio: see Table 3. The terms Hmajor and Hminor are used to indicate separated
proton resonance for the major or the minor diastereomer.
b Mixture of 4 diastereomers.
Synthesis 2000, No. 9, 1279–1290 ISSN 0039-7881 © Thieme Stuttgart · New York