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. Author manuscript; available in PMC: 2018 Nov 14.
Published in final edited form as: Tetrahedron Lett. 2002 Jul 17;43(32):5621–5624. doi: 10.1016/S0040-4039(02)01113-9

Table 1.

Aldol reaction of ester 2 with representative aldehydes

Entry Aldehyde Compda Yield (%)b syn:anti (3/4)c
1 Me2CHCHO 3a 89 90:10
2 Me2CHCH2CHO 3b 93 95:5
3 trans-PhCH=CHCHO 3c 89 96:4
4 PhCHO 3d 94 88:12
5 Me(CH2)6CHO 3e 96 82:18
6 Ph-C≡C-CHO 3f 86 36:64d
7 BnOCH2CHO 3g 74 99:1
8 BnOCH2CH2CHO 3h 81 99:1
9 graphic file with name nihms-993876-t0001.jpg 3i 77 99:1
10 graphic file with name nihms-993876-t0002.jpg 3j 82 34:66d
a

Major isolated product.

b

Isolated yield after chromatography.

c

Ratios determined by 1H MR and HPLC analysis before and after chromatography. Reaction time=1.5–2 h.

d

Ratio after removal of chiral auxiliary.