Brønsted acid catalyzed regioselective aza-Ferrier reaction: a novel synthetic method for alpha-(N-Boc-2-pyrrolidinyl) aldehydes.
The 1,4-elimination reaction of (Z)-N-Boc-2-(4-methoxy-2-alkenyloxy)pyrrolidines is shown to proceed with high (1E,3E)-stereoselectivity to afford N-Boc-2-(1,3-dienyloxy)pyrrolidines; the Brønsted acid catalyzed aza-Ferrier reaction of the N-Boc-2-(1,3-dienyloxy)pyrrolidines (3) provides alpha-(N-Boc-2-pyrrolidinyl) aldehydes in excellent yields with high alpha-regioselectivities.
Tayama
Eiji
E
Graduate School of Science and Technology, Niigata University, Niigata 950-2181, Japan. tayama@gs.niigata-u.ac.jp
Otoyama
Seijun
S
Isaka
Wataru
W