A Unified Strategy for the Asymmetric Synthesis of Highly Substituted 1,2-Amino Alcohols Leading to Highly Substituted Bisoxazoline Ligands
- Award ID(s):
- 1900617
- NSF-PAR ID:
- 10237403
- Date Published:
- Journal Name:
- The Journal of Organic Chemistry
- Volume:
- 86
- Issue:
- 4
- ISSN:
- 0022-3263
- Page Range / eLocation ID:
- 3490 to 3534
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
More Like this
-
An auto-tandem catalytic, branched-selective rearrangement of substituted N-alloc-N-allyl ynamides was developed. This reaction provides ready access to complex quaternary nitrile products with vinylogous stereocentres in excellent diastereoselectivity, including contiguous all-carbon quaternary centres. The stereochemical outcome is determined via a Pd(0) catalysed dipolar ketenimine aza-Claisen rearrangement and computational studies exemplify the key role ligand geometry plays.more » « less
-
Transformation of multifunctional materials with control over site-selectivity and chemical diversity remains challenging. Herein, we present a metal-free, one-pot strategy for the defluorophosphorylation of polyfluoroalkyl peroxides that enables expedient construction of structurally diverse phosphoryl-containing heterocyclic libraries. By judicious choice of reaction conditions, C 3,4-diphosphoryl furans and C 4-monophosphoryl furans can be easily accessed. In addition, synthetic derivatization of the obtained organophosphorus heteroarenes to value-added monodentate and bidentate phosphines has been demonstrated. Mechanistic studies revealed that regioselective defluorophosphorylation allows divergent product formation in two reaction modes.more » « less