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

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.

SUBMITTER: Nelson HM

PROVIDER: S-EPMC4251561 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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

Nelson H M HM Patel J S JS Shunatona H P HP Toste F D FD

Chemical science 20150101 1

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. ...[more]

PMID: 25485073

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