Premium
Asymmetric Aza‐Morita–Baylis–Hillman Reactions of Alkyl Vinyl Ketones with N ‐Protected Imines or In Situ Generated N ‐Protected Imines
Author(s) -
Guan XiaoYang,
Wei Yin,
Shi Min
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000496
Subject(s) - chemistry , dabco , enantioselective synthesis , methyl vinyl ketone , adduct , methylene , catalysis , alkyl , medicinal chemistry , baylis–hillman reaction , organocatalysis , ketone , organic chemistry , amine gas treating
DABCO‐catalyzed aza‐MBH reactions of N ‐Boc imines with MVK and EVK have been thoroughly investigated in the paper. The asymmetric version of this aza‐MBH reaction was also systematically investigated by using a chiral amine or a chiral phosphane catalyst. It was found that most of the N ‐protected imines are suitable substrates under the mild reaction conditions and are able to give the corresponding adducts in moderate yields with high ee values. The TQO‐ or LB1‐catalyzed aza‐MBH reactions of N ‐protected α‐amidoalkyl phenyl sulfones or α‐amidoalkyl p ‐tolyl sulfones with MVK could be well conducted, which provides a facile and direct route to obtain highly enantioselective aza‐MBH adducts. The Boc protecting group of the aza‐MBH product could be easily removed under acidic conditions to give the corresponding α‐methylene‐β‐amino ketone or α‐methylene‐β‐amino alcohol derivatives in good yields.