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Beilstein J. Org. Chem. 2008, 4, No. 38, doi:10.3762/bjoc.4.38
Graphical Abstract
Scheme 1: Cyclopropylmethyl–homoallyl and nortricyclyl–norbornenyl radical systems.
Scheme 2: Deoxygenation-rearrangement-electrophile trapping.
Figure 1: Radical SOMO/α-nitrogen lone-pair interaction in the rearranged radical 7.
Figure 2: Other products obtained from xanthate 5 by tandem deoxygenation–rearrangement–electrophile trapping....
Scheme 3: Asymmetric hydroboration–oxidation of alkenes 14, 16 and 18.
Scheme 4: Deoxygenation–rearrangement–isomerisation of xanthates 20 and 23.
Scheme 5: Deoxygenation–rearrangement–electrophile trapping of xanthates 20 and 23.
Scheme 6: 2-Azabenzonorbornene as a masked pyrrolidine.
Scheme 7: Ring-opening–hydration–oxidation of azacycle 8.
Scheme 8: Preparation of trisubstituted pyrrolidine (+)-36.
Scheme 9: Preparation of pyrrolidine diester (+)-35 from Vince’s lactam 37.
Scheme 10: Acid-catalysed ring-opening–oxidation of azacycle (+)-8.
Scheme 11: Birch reduction of (+)-8 and 10.