Journal
ORGANIC LETTERS
Volume 23, Issue 16, Pages 6372-6376Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02179
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Funding
- Irish Research Council (IRC) [GOIPG/2014/343]
- National Science Foundation [CHE-1764328, OCI-1053575]
- Irish Research Council (IRC) [GOIPG/2014/343] Funding Source: Irish Research Council (IRC)
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The study demonstrates the stereoselective formation of 5 contiguous chiral centers in a single pot reaction using aldol, aldol-Tishchenko reaction of N-tert-butyl sulfinimines. The researchers synthesized a series of cyclic and acyclic 3-amino-1,5-diol derivatives with high yields and excellent diastereoselectivities. The investigation supports two reversible aldol steps and a remarkably selective, irreversible Tishchenko reduction.
The stereoselective formation of 5 contiguous chiral centers in a single pot reaction is demonstrated using an aldol, aldol-Tishchenko reaction of N-tert-butyl sulfinimines. One diastereoisomer (from 32 possibilities) predominates, and a series of cyclic and acyclic 3-amino-1,5-diol derivatives are synthesized in good yields (up to 80%) and excellent diastereoselectivities (up to >98:2 dr). Investigations support two reversible aldol steps, and multiple intermediates which are funnelled through a remarkably selective, irreversible, Tishchenko reduction, in a Curtin-Hammett phenomenon. DFT calculations using a disolvated (THF) model reveal the factors controlling stereoselectivity in the final irreversible Tishchenko step.
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