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. Author manuscript; available in PMC: 2019 Jul 12.
Published in final edited form as: Tetrahedron Lett. 2001 Feb 28;42(7):1227ā€“1231. doi: 10.1016/S0040-4039(00)02227-9

Table 1.

Aldol reaction of various esters 2aā€“c with representative aldehydes

Entry Ester Aldehyde Compda % Yieldb Syn:Anti (5/4)c
1. 2a BnOCH2CHO 5a 80 98: 2
2. 2a BnO(CH2)2CHO 5b 81 97: 3
3. 2a BnO(CH2)3CHO 5c 58 91: 9
4. 2b BnOCH2CHO 5d 63 97; 3
5. 2c BnOCH2CHO 5e 60 96: 4
6. 2a graphic file with name nihms-1024689-t0005.jpg 5f 84 99: 1
7. 2a graphic file with name nihms-1024689-t0006.jpg 4g 59 30: 70d
8. 2a graphic file with name nihms-1024689-t0007.jpg 5h 78 99: 1
9. 2a graphic file with name nihms-1024689-t0001.jpg 5i 81 83: 17d
10. 2a iBuCHO 4j 70 30: 70d
11. 2a Ph-C= C-CHO 4k 60 15: 85d
a

Major isolated product; 5a (R=Me, R1=CH2OBn); 5b (R=Me, R1=(CH2)2OBn); 5c (R=Me, R1=(CH2)3OBn); 5d (R=Bn, R1=CH2OBn); 5e (R=iBu, R1=CH2OBn); 4j and 5j (R=Me, R1=iBu); 4k and 5k (R=Me, R1= Cā‰” C-Ph);

b

Isolated yield after chromatography.

c

Ratios determined by 1H-NMR and HPLC analysis before and after chromatography. Reaction time = 1.5ā€“2 h;

d

Ratio after removal of chiral auxiliary.