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. 2014 Aug 26;10:1991–1998. doi: 10.3762/bjoc.10.207

Table 2.

Synthesis of 2-benzyltryptophans 3a–j.a

graphic file with name Beilstein_J_Org_Chem-10-1991-i002.jpg

Entry Indole Tryptophan Time (h) Yield (%)b

1 Inline graphic
1a
Inline graphic
3a
24 70
2 Inline graphic
1b
Inline graphic
3b
16 74
3 Inline graphic
1c
Inline graphic
3c
48 53
4 Inline graphic
1d
Inline graphic
3d
72 NR
5 Inline graphic
1e
Inline graphic
3e
72 NR
6 Inline graphic
1f
Inline graphic
3f
72 11
7 Inline graphic
1g
Inline graphic
3g
72 NR
8 Inline graphic
1h
Inline graphic
3h
24 67
9 Inline graphic
1i
Inline graphic
3i
48 51
10c Inline graphic
1a
Inline graphic
3j
24 48

aReaction Conditions: 1a–i (0.25 mmol), 2a (0.3 mmol), EtAlCl2 (0.5 mmol), CH2Cl2 (2.5 mL), rt. bYields of the isolated products after column chromatography. cMethyl 2-phthalimidoacrylate (2b) was used. NR, no reaction.