Highly Diastereoselective Oxy-Michael Additions of Enantiopure δ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols

Nicola Adderley; David Buchanan; Darren Dixon; Dramane Lainé

doi:10.1002/anie.200352007

Highly Diastereoselective Oxy-Michael Additions of Enantiopure δ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols

Nicola Adderley, David Buchanan, Darren Dixon, Dramane Lainé

Applied Health Research

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

46 Citations (Scopus)

Abstract

The “naked” alkoxide 1 of (S)‐6‐methyl‐δ‐lactol acts as an excellent chiral hydroxide equivalent in highly diastereoselective oxy‐Michael additions to nitroalkenes (see scheme). The excellent stereoinduction arises from what becomes a superb protecting group in the resulting 1,2‐amino alcohol products. R1=alkyl, aryl, furanyl, thiophenyl; R2,R3=-(CH2)3CHCH3O-.

Original language	English
Pages (from-to)	4241
Number of pages	4244
Journal	Angewandte Chemie (International Edition)
Volume	42
Issue number	35
DOIs	https://doi.org/10.1002/anie.200352007
Publication status	Published - 15 Sept 2003

Keywords

Amino alcohols
diastereoselectivity
lactols
Michael addition
nitroalkenes

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10.1002/anie.200352007

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title = "Highly Diastereoselective Oxy-Michael Additions of Enantiopure δ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols",

abstract = "The “naked” alkoxide 1 of (S)‐6‐methyl‐δ‐lactol acts as an excellent chiral hydroxide equivalent in highly diastereoselective oxy‐Michael additions to nitroalkenes (see scheme). The excellent stereoinduction arises from what becomes a superb protecting group in the resulting 1,2‐amino alcohol products. R1=alkyl, aryl, furanyl, thiophenyl; R2,R3=-(CH2)3CHCH3O-. ",

keywords = "Amino alcohols, diastereoselectivity, lactols, Michael addition, nitroalkenes",

author = "Nicola Adderley and David Buchanan and Darren Dixon and Dramane Lain{\'e}",

year = "2003",

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language = "English",

volume = "42",

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T1 - Highly Diastereoselective Oxy-Michael Additions of Enantiopure δ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols

AU - Adderley, Nicola

AU - Buchanan, David

AU - Dixon, Darren

AU - Lainé, Dramane

PY - 2003/9/15

Y1 - 2003/9/15

N2 - The “naked” alkoxide 1 of (S)‐6‐methyl‐δ‐lactol acts as an excellent chiral hydroxide equivalent in highly diastereoselective oxy‐Michael additions to nitroalkenes (see scheme). The excellent stereoinduction arises from what becomes a superb protecting group in the resulting 1,2‐amino alcohol products. R1=alkyl, aryl, furanyl, thiophenyl; R2,R3=-(CH2)3CHCH3O-.

AB - The “naked” alkoxide 1 of (S)‐6‐methyl‐δ‐lactol acts as an excellent chiral hydroxide equivalent in highly diastereoselective oxy‐Michael additions to nitroalkenes (see scheme). The excellent stereoinduction arises from what becomes a superb protecting group in the resulting 1,2‐amino alcohol products. R1=alkyl, aryl, furanyl, thiophenyl; R2,R3=-(CH2)3CHCH3O-.

KW - Amino alcohols

KW - diastereoselectivity

KW - lactols

KW - Michael addition

KW - nitroalkenes

U2 - 10.1002/anie.200352007

DO - 10.1002/anie.200352007

M3 - Article

SN - 1433-7851

VL - 42

SP - 4241

JO - Angewandte Chemie (International Edition)

JF - Angewandte Chemie (International Edition)

IS - 35

ER -

Highly Diastereoselective Oxy-Michael Additions of Enantiopure δ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols

Abstract

Keywords

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