Squaramide-Catalyzed Enantioselective Michael Addition of Masked Acyl Cyanides to Substituted Enones
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, cilt.135, sa.43, ss.16050-16053, 2013 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 135 Sayı: 43
- Basım Tarihi: 2013
- Doi Numarası: 10.1021/ja409012q
- Dergi Adı: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
- Sayfa Sayıları: ss.16050-16053
- Orta Doğu Teknik Üniversitesi Adresli: Hayır
Özet
Masked acyl cyanide (MAC) reagents are shown to be effective umpolung synthons for enantioselective Michael addition to substituted enones. The reactions are catalyzed by chiral squaramides and afford adducts in high yields (90-99%) and with excellent enantioselectivities (85-98%). The addition products are unmasked to produce dicyanohydrins that, upon treatment with a variety of nucleophiles, provide gamma-keto acids, esters, and amides. The use of this umpolung synthon has enabled, in enantiomerically enriched form, the first total synthesis of the prenylated phenol (+)-fornicin C.