Highly stereospecific arylation of (S)proline and complementary highly diastereoselective reduction of the α-amino ketone. Asymmetric synthesis of (1S,2′S)- and (1R,2′S)-phenyl(2′-pyrrolidinyl)methanol

Kenso Soai; Atsuhiro Ookawa

doi:10.1039/C39860000412

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Highly stereospecific arylation of (S)proline and complementary highly diastereoselective reduction of the α-amino ketone. Asymmetric synthesis of (1S,2′S)- and (1R,2′S)-phenyl(2′-pyrrolidinyl)methanol

Kenso Soai and Atsuhiro Ookawa

Abstract

Both optically active threo- and erythro-phenyl(2′-pyrrolidinyl)methanol (93–100% enantiomeric excess, 100% diastereoisomeric excess) were synthesised from (S)-proline by a stereospecific arylation and the subsequent complementary diastereoselective reduction of the α-amino ketone.

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DOI: https://doi.org/10.1039/C39860000412
Article type: Paper

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J. Chem. Soc., Chem. Commun., 1986, 412-413

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Highly stereospecific arylation of (S)proline and complementary highly diastereoselective reduction of the α-amino ketone. Asymmetric synthesis of (1S,2′S)- and (1R,2′S)-phenyl(2′-pyrrolidinyl)methanol

K. Soai and A. Ookawa, J. Chem. Soc., Chem. Commun., 1986, 412 DOI: 10.1039/C39860000412

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Journal of the Chemical Society, Chemical Communications

Highly stereospecific arylation of (S)proline and complementary highly diastereoselective reduction of the α-amino ketone. Asymmetric synthesis of (1S,2′S)- and (1R,2′S)-phenyl(2′-pyrrolidinyl)methanol

Abstract

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Highly stereospecific arylation of (S)proline and complementary highly diastereoselective reduction of the α-amino ketone. Asymmetric synthesis of (1S,2′S)- and (1R,2′S)-phenyl(2′-pyrrolidinyl)methanol

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