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Published May 25, 2016 | Accepted Version + Supplemental Material
Journal Article Open

A mild and efficient approach to enantioenriched α-hydroxyethyl α,β-unsaturated δ-lactams


A straightforward approach toward enantioenriched α-substituted α,β-unsaturated δ-lactams is described. Although a considerable number of approaches toward α,β-unsaturated δ-lactams have been reported, there are relatively few examples of enantioenriched α,δ-disubstituted α,β-unsaturated δ-lactams formation. The δ-stereocenter was formed by addition of allylmagnesium bromide to an N-tert-butylsulfinyl imine. The α,β-unsaturated δ-lactam was furnished by ring-closing metathesis. Although Baylis–Hillman chemistry failed on this cyclic compound, introduction of the hydroxyethyl group prior to ring-closing metathesis was successful. A Baylis–Hillman reaction was used to introduce the substituent at the α-position of the α,β-unsaturated lactam.

Additional Information

© 2016 Elsevier Ltd. Received 15 March 2016; Revised 5 April 2016; Accepted 7 April 2016; Available online 9 April 2016. The authors wish to thank the NIH-NIGMS (R01GM080269-01), Amgen, and Caltech for financial support. S.-J.H thanks Fulbright (Foreign Student Program, No. 15111120) and the Ilju Foundation of Education & Culture (Pre-doctoral Research Fellowship) for financial support. Dr. Mona Shahgholi (Caltech) and Naseem Torian (Caltech) are acknowledged for high-resolution mass spectrometry assistance.

Attached Files

Accepted Version - nihms-781429.pdf

Supplemental Material - mmc1.pdf


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