Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase

Azusa Kondoh; Masafumi Oishi; Tadahiro Takeda; Masahiro Terada

doi:10.1002/anie.201508178

Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase

Azusa Kondoh, Masafumi Oishi, Tadahiro Takeda, Masahiro Terada

Research output: Contribution to journal › Article › peer-review

49 Citations (Scopus)

Abstract

A chiral bis(guanidino)iminophosphorane catalyzes enantioselective addition reactions of a 1,3-dithiane derivative as a pronucleophile. The chiral uncharged organosuperbase facilitates the addition of benzyloxycarbonyl-1,3-dithiane to aromatic N-Boc-protected imines to provide optically active α-amino-1,3-dithiane derivatives, which are valuable versatile building blocks in organic synthesis.

Original language	English
Pages (from-to)	15836-15839
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	52
DOIs	https://doi.org/10.1002/anie.201508178
Publication status	Published - 2015 Dec 21

Keywords

1,3-dithianes
asymmetric catalysis
organocatalysis
organosuperbases
phosphazenes

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10.1002/anie.201508178

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title = "Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase",

abstract = "A chiral bis(guanidino)iminophosphorane catalyzes enantioselective addition reactions of a 1,3-dithiane derivative as a pronucleophile. The chiral uncharged organosuperbase facilitates the addition of benzyloxycarbonyl-1,3-dithiane to aromatic N-Boc-protected imines to provide optically active α-amino-1,3-dithiane derivatives, which are valuable versatile building blocks in organic synthesis.",

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author = "Azusa Kondoh and Masafumi Oishi and Tadahiro Takeda and Masahiro Terada",

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T1 - Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase

AU - Kondoh, Azusa

AU - Oishi, Masafumi

AU - Takeda, Tadahiro

AU - Terada, Masahiro

PY - 2015/12/21

Y1 - 2015/12/21

N2 - A chiral bis(guanidino)iminophosphorane catalyzes enantioselective addition reactions of a 1,3-dithiane derivative as a pronucleophile. The chiral uncharged organosuperbase facilitates the addition of benzyloxycarbonyl-1,3-dithiane to aromatic N-Boc-protected imines to provide optically active α-amino-1,3-dithiane derivatives, which are valuable versatile building blocks in organic synthesis.

AB - A chiral bis(guanidino)iminophosphorane catalyzes enantioselective addition reactions of a 1,3-dithiane derivative as a pronucleophile. The chiral uncharged organosuperbase facilitates the addition of benzyloxycarbonyl-1,3-dithiane to aromatic N-Boc-protected imines to provide optically active α-amino-1,3-dithiane derivatives, which are valuable versatile building blocks in organic synthesis.

KW - 1,3-dithianes

KW - asymmetric catalysis

KW - organocatalysis

KW - organosuperbases

KW - phosphazenes

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Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase

Abstract

Keywords

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