Sulfone chemistry for the synthesis of C-branched pyrrolidines

The synthesis of a C-branched homopyrrolidinol has been achieved by making use of the reactivity of the sulfone group in four different ways. The stereochemistry of the two compounds has been established by X-ray diffraction analysis.

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(3S,3aS,4S,5R)-3-Phenylsulfonyl-3a-phenylsulfonylmethyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazoleC22H25NO7S2E.e,d.e.: >95% (NMR)[α]D20=+8.2 (c 0.22, CHCl3)Source of chirality: natural productAbsolute configuration: (3S,3aS,4S,5R)

(2S,3aS,4S,5R)-3-Phenylsulfonyl-3a-phenylsulfonylmethyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazoleC22H25NO7S2E.e,d.e.: >95% (NMR)[α]D20=-104.7 (c 0.46, CHCl3)Source of chirality: natural productAbsolute configuration: (2S,3aS,4S,5R)

(2R,3aS,4S,5R)-3-Phenylsulfonyl-3a-phenylsulfonylmethyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazoleC22H25NO7S2E.e,d.e.: >95% (NMR)[α]D20=-45.2 (c 0.46, CHCl3)Source of chirality: natural productAbsolute configuration: (2R,3aS,4S,5R)

(2R,3aR,4S,5R)-3-Phenylsulfonyl-3a-phenylsulfonylmethyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazoleC22H25NO7S2E.e,d.e.: >95% (NMR)[α]D20=-55.7 (c 1.24, CHCl3)Source of chirality: natural productAbsolute configuration: (2R,3aR,4S,5R)

(2S,3S,4R)-2-Hydroxyethyl-2-phenylsulfonylmethyl-3,4-isopropylidenedioxypyrrolidineC16H23NO5SE.e,d.e.: >95% (NMR)[α]D20=-11.0 (c 0.59, MeOH)Source of chirality: natural productAbsolute configuration: (2S,3S,4R)

(2R,3S,4R)-2-Hydroxyethyl-2-phenylsulfonylmethyl-3,4-isopropylidenedioxypyrrolidineC16H23NO5SE.e,d.e.: >95% (NMR)[α]D20=-22.5 (c 1.03, MeOH)Source of chirality: natural productAbsolute configuration: (2R,3S,4R)

(2S,3S,4R)-2-Hydroxyethyl-2-methyl-3,4-isopropylidenedioxypyrrolidineC10H19NO3E.e,d.e.: >95% (NMR)[α]D20=-12.3 (c 0.30, MeOH)Source of chirality: natural productAbsolute configuration: (2S,3S,4R)

(2S,3S,4R)-2-Hydroxyethyl-2-methyl-3,4-dihydroxypyrrolidineC7H13NO3E.e,d.e.: >95% (NMR)[α]D20=-32.9 (c 0.38, H2O)Source of chirality: natural productAbsolute configuration: (2S,3S,4R)