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. 2015 Jan 1;6(1):170-173.
doi: 10.1039/C4SC02494J.

Enantioselective α-Amination Enabled by a BINAM-Derived Phase-Transfer Catalyst

H M Nelson  1 , J S Patel  1 , H P Shunatona  1 , F D Toste  1
Affiliations

Enantioselective α-Amination Enabled by a BINAM-Derived Phase-Transfer Catalyst

H M Nelson et al. Chem Sci. .

Abstract

Chiral anion phase-transfer of aryldiazonium cations was utilized to achieve highly enantioselective α-amination of carbonyl compounds. A broad scope of indanone- and benzosuberone-derived substrates was amenable to this strategy. Critical to obtaining high levels of enantioselectivity was the use of BINAM-derived phosphoric acids. The utility of this transformation was demonstrated through facile conversion of diazene products to valuable α-amino acid derivatives.

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Figures

Fig. 1
Fig. 1. (a) Chiral anion phase-transfer concept. (b) Application to α-amination. (c) Biologically active amino-indanone derivatives.
Scheme 1
Scheme 1. Diazenation of additional substrates.
Scheme 2
Scheme 2. Applications of diazene products.
See this image and copyright information in PMC

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