Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction

• Koichiro Miyazaki,
• Yu Yamane,
• Ryuichiro Yo,
• Hidemitsu Uno and
• Akio Kamimura

Beilstein J. Org. Chem. 2013, 9, 1326–1332, doi:10.3762/bjoc.9.149

• : bicyclodihydrosilole; free radical; radical cascade reaction; SHi reaction; tris(trimethylsilyl)silane; Introduction Radical cyclization occupies a unique position in organic synthesis because it is a useful reaction for the construction of cyclic molecules [1][2][3][4][5][6][7][8][9][10]. The radical cascade

• -propargylation [29][30]. We first optimized the reaction conditions. The results are summarized in Table 1. Treatment of 1 with (Me3Si)3SiH in the presence of catalytic amounts of AIBN at 110 °C resulted in the formation of the desired bicyclodihydrosilole 2a in 14% yield (Table 1, entry 1). The use of one