(1S,2S)-1-Amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene: a new chiral auxiliary for asymmetric Reformatsky reactions

(1S,2S)-1-Amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene, synthesized via a chemoenzymatic approach from naphthalene, has been successfully used as a chiral auxiliary in Reformatsky-type reactions between the corresponding α-bromoacyloxazolidinone and carbonyl compounds.

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(4S,5S)-Tetrahydronaphthalene-(1,2-d)-oxazolidin-2-oneC11H11NO2[α]D = +14.0 (c 1.0, CHCl3)Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

N-(α-Bromoacetyl)-(4S,5S)-tetrahydronaphthalene-(1,2-d)-oxazolidin-2-oneC13H12BrNO3[α]D = +272 (c 1.0, CHCl3)Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

(1S,2S)-1-p-Tolylsulfonamido-2-hydroxy-1,2,3,4-tetrahydronaphthaleneC17H19NO3S[α]D = +33.8 (c 1.0, CHCl3)Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

(1S,2S)-1-p-Tolylsulfonamido-2-(α-bromoacetyl)-1,2,3,4-tetrahydronaphthaleneC19H20BrNO4S[α]D = +35.1 (c 1.0, CHCl3)Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

N-[(3R)-3-Hydroxy-4-methyl-pentanoyl]-(4S,5S)-tetrahydronaphthalene-(1,2-d)-oxazolidin-2-oneC17H21NO4[α]D = +208.4 (c 1.0, CHCl3)De >98%Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

N-[(3S)-3-Hydroxy-5-phenyl-pentanoyl]-(4S,5S)-tetrahydronaphthalene-(1,2-d)-oxazolidin-2-oneC22H23NO4[α]D = +271.1 (c 1.66, CHCl3)De >98%Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

N-[(3R)-3-Hydroxy-4,4-dimethyl-pentanoyl]-(4S,5S)- tetrahydronaphthalene-(1,2-d)-oxazolidin-2-oneC18H23NO4[α]D = +290.26 (c 0.75, CHCl3)De >98%Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

N-[(3R)-3-Hydroxy-4-ethyl-hexanoyl]-(4S,5S)-tetrahydronaphthalene-(1,2-d)-oxazolidin-2-oneC19H35NO4[α]D = +309.3 (c 1.1, CHCl3)De >98%Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

N-[(3R)-3-Hydroxy-3-phenyl-pentanoyl]-(4S,5S)-tetrahydronaphthalene-(1,2-d)-oxazolidin-2-oneC20H19NO4[α]D = +284.0 (c 1, CHCl3)De >98%Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

N-[(3S)-3-Hydroxy-4-methyl-pentanoyl]-(4S,5S)-tetrahydronaphthalene-(1,2-d)-oxazolidin-2-oneC17H21NO4[α]D = +150.5 (c 0.8, CHCl3)Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene

N-[(3R)-3-Hydroxy-5-phenyl-pentanoyl]-(4S,5S)-tetrahydronaphthalene-(1,2-d)-oxazolidin-2-oneC22H23NO4[α]D = +177.81 (c 0.9, CHCl3)Source of chirality: (1R,2S)-1,2-dihydroxy-1,2-dihydronaphthalene