Highly efficient photochemical addition of tertiary amines to electron deficient alkenes. Diastereoselective addition to (5R)-5-Menthyloxy-2[5H]-furanone
S. Bertrand et al., Highly efficient photochemical addition of tertiary amines to electron deficient alkenes. Diastereoselective addition to (5R)-5-Menthyloxy-2[5H]-furanone, TETRAHEDR L, 40(16), 1999, pp. 3169-3172
Tertiary amines derived from pyrrolidines can be added very efficiently (is
olated yields up to 94%) to (5R)-5-mentyloxy-2[5H]-furanone. The addition,
which follows a radical chain mechanism initiated by a photoinitiated elect
ron transfer (PET) from the tertiary amine to the excited aromatic ketone,
occurs with a complete facial selectivity on the furanone ring. The method
can be generalized to the addition of tertiary amines and N-protected secon
dary amines to electron deficient alkenes. (C) 1999 Published by Elsevier S
cience Ltd. Ail rights reserved.