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Lewis-Base-Catalyzed Reductive Aldol Reaction To Access Quaternary Carbons
A synthetic method for the efficient construction of β-hydroxylactones and lactams bearing α-quaternary carbon centers is described. This transformation relies on an electronically differentiated Lewis base catalyst, which is uniquely capable of promoting a reductive aldol reaction of α,α-disubstituted and α,α,β-trisubstituted enones. This approach provides a valuable synthetic alternative for carbon–carbon bond formation in complex molecular settings due to its orthogonal reactivity compared to that of traditional aldol reactions. Based on this method described herein, lactones, lactams, and morpholine amides bearing α-quaternary carbon centers are accessible in yields up to 85% and 50:1 dr.
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- Award ID(s):
- 1654223
- PAR ID:
- 10341812
- Date Published:
- Journal Name:
- Organic letters
- Volume:
- 20
- Issue:
- 9
- ISSN:
- 1523-7060
- Page Range / eLocation ID:
- 2580-2584
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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- Free Publicly Accessible Full Text
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/doi.org/10.1021/acs.orglett.8b00507
