TY - JOUR
T1 - Syn selective vinylogous mukaiyama aldol reaction using Z,EVinylketene N,O-acetal with acetals
AU - Sagawa, Naoya
AU - Moriya, Hiroki
AU - Hosokawa, Seijiro
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/1/6
Y1 - 2017/1/6
N2 - Stereoselective vinylogous Mukaiyama aldol reactions using the Z,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary, derived from (E)-3-pentenoic acid and Lvaline, have been achieved. The reaction proceeded smoothly to give a syn adduct in high stereoselectivity. Since the products possess structures including δ-alkoxy-γ-methyl-α,β-unsaturated imide, this reaction would be applicable to synthesize polyketides in a short procedure.
AB - Stereoselective vinylogous Mukaiyama aldol reactions using the Z,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary, derived from (E)-3-pentenoic acid and Lvaline, have been achieved. The reaction proceeded smoothly to give a syn adduct in high stereoselectivity. Since the products possess structures including δ-alkoxy-γ-methyl-α,β-unsaturated imide, this reaction would be applicable to synthesize polyketides in a short procedure.
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U2 - 10.1021/acs.orglett.6b03549
DO - 10.1021/acs.orglett.6b03549
M3 - Article
C2 - 28001414
AN - SCOPUS:85034782460
SN - 1523-7060
VL - 19
SP - 250
EP - 253
JO - Organic Letters
JF - Organic Letters
IS - 1
ER -