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. 2021 May 10;17:1048–1085. doi: 10.3762/bjoc.17.84

Table 3.

Synthesis of chromenes by the 1,4-addition of boronic acids to β-(2-hydroxyaryl)enones [34].

graphic file with name Beilstein_J_Org_Chem-17-1048-i003.jpg

entry R1 R2 R3 Ar additive (equiv) yield A + B (%)
ratio A/B
yield C (%) ee C (%)

1 H Me Me Ph 99 (1:13) 90 96
2 H Me Me 4-MeO-C6H4 AgBF4 (0.1) 96 (1:13) 90 97
3 H Me Me 3-MeO-C6H4 AgBF4 (0.1) 96 (1:13) 94 97
4 H Me Me 3,4-(CH2O2)-C6H3 AgBF4 (0.1) 99 (1:16) 89 98
5 H Me Me 4-Me-C6H4 99 (1:13) 94 97
6 H Me Me 4-Ac-C6H4 AgBF4 (0.1) 99 (1:16) 90 96
7 H H Ph Ph 99 (2:1) 92 99
8 H OMe Me Ph 99 (1:16) 94 95
9 t-Bu t-Bu Me Ph 94 (1:99) 90