Lithiated β-aminoalkyl sulfones as mono and dinucleophiles in the preparation of nitrogen heterocycles: Application to the synthesis of capsazepine

Alonso, Diego A.; Costa, Ana; Mancheño, Balbino; Nájera, Carmén

doi:10.1016/s0040-4020(97)00163-4

Cited by 39 publications

(19 citation statements)

References 35 publications

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“…288 The endo lactam was obtained quantitatively during removal of the benzyl group, whereas amino lactam 106 was more resistant to condensation. However, the corresponding lactam 107-exo was generated in a separate step after treatment of the amino ester with LDA.…”

Section: Synthesis Of Bridged Lactams With N–(co) Bond On Two-carbmentioning

confidence: 99%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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CONTENTS 1. Introduction 5702 2. General Properties of Bridged Lactams 5703 2.1. Distortion Parameters of Bridged Lactams 5703 2.2. Bond Lengths of Bridged Lactams 5703 2.3. Spectroscopic Properties of Bridged Lactams 5703 2.4. Analogy of Bridged Lactams to Bridgehead Olefins 5704 2.5. Chemical and Biological Significance of Distorted Amides 5704 3. Synthesis of Historically Important Bridged Lactams 5704 3.1. Quinuclidone Derivatives 5704 3.2. Adamantanone Derivatives 5707 4. Synthesis of Bridged Lactams with the N−(CO) Bond on a Two-Carbon or Larger Bridge, ([m. (≥2).n] Type) 5708 4.1. Condensation Reactions Forming the N− C(O) Bond 5708 4.2. Heck Reactions 5711 4.3. Diels−Alder Reactions 5712 4.4. Carbene Insertion Reactions 5713 4.5. Reactions via Radical Intermediates 5714 4.6. Miscellaneous Examples 5714 5. Synthesis of Bridged Lactams with the N−(CO) Bond on a One-Carbon Bridge, ([m.1.n] Type) 5715 5.1. Carbene Insertion Reactions 5715 5.2. Schmidt Reactions 5716 5.3.

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Section: Synthesis Of Bridged Lactams With N–(co) Bond On Two-carbmentioning

confidence: 99%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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“…A two-carbon elongation for preparing a,b-unsaturated ester 11 was accomplished by Swern oxidation and Wittig olefination under a one-pot standard condition. 6 A conversion of a,b-unsaturated ester 11 to a,b-unsaturated aldehyde 13 was afforded via alane reduction (freshly prepared from the combination of lithium aluminum hydride and aluminum chloride) of 9 (±)-trachelanthamidine (4 7 In order to prevent the ring-opening of the pyrrolizidine skeleton, we next turn our attention to examine the reduction of pyroglutamate 11 as shown in Scheme III. For the reduction of pyroglutamate 11 with lithium aluminum hydride, two alcohols 16a and 16b were generated in the ratio of 1:2.…”

Section: Resultsmentioning

confidence: 99%

Formal Synthesis of (±)‐Trachelanthamidine via Base‐Induced Formal [3+2] Annulation and Intramolecular Cyclization

Hsu

Chang

2006

J Chinese Chemical Soc

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“…[3] Additionally, they readily undergo electrophilic substitution in the a postion and have, for instance, been used as intermediates in the synthesis of aamino acids, [4,5] amino alcohols, [6] substituted uridines and adenosines, [7] alkaloids, [8] b-lactams, [9] and nitrogen heterocycles. [10,11] As early as the 1960s Stirling and McDowell investigated the kinetics of the intermolecular addition of achiral amines to alkenyl sulfones. [12] Today, there exist several procedures for intramolecular [6,8,13] and intermolecular [7,10,11,14] aza-Michael additions to alkenyl sulfones.…”

Section: Enantioselective Synthesis Of B-aminomentioning

confidence: 99%

“…[10,11] As early as the 1960s Stirling and McDowell investigated the kinetics of the intermolecular addition of achiral amines to alkenyl sulfones. [12] Today, there exist several procedures for intramolecular [6,8,13] and intermolecular [7,10,11,14] aza-Michael additions to alkenyl sulfones. However, to our knowledge the enantioselective aza-Michael addition with a nitrogen nucleophile bearing chirality information, which may subsequently be cleaved, has not been described.…”

Section: Enantioselective Synthesis Of B-aminomentioning

confidence: 99%

Enantioselective Synthesis of -Amino Sulfones by aza-Michael Addition to Alkenyl Sulfones

Enders¹,

Müller²,

Raabe³

1999

Angew. Chem. Int. Ed.

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Enantioselective Synthesis of β-Amino Sulfones by Aza-Michael Addition to Alkenyl Sulfones.-An efficient approach to synthetically valuable and enantiopure β-amino sulfones (V) is presented involving the asymmetric aza-Michael addition of (E)-alkenyl sulfones (I) to amines (II) and (VI) containing a chiral auxiliary. Although diastereoselectivities are only moderate, the isomers can be separated chromatographically to yield adducts (III) and (VII) in over 96% selectivity. Removal of the chiral auxiliary with BH 3 ·THF complex and subsequent Boc protection affords the N-Boc-β-amino sulfones (V) in excellent optical purity. Both enantiomers are accessible using either amine (II) or (VI) in the aza-Michael addition.

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Lithiated β-aminoalkyl sulfones as mono and dinucleophiles in the preparation of nitrogen heterocycles: Application to the synthesis of capsazepine

Cited by 39 publications

References 35 publications

Chemistry of Bridged Lactams and Related Heterocycles

Chemistry of Bridged Lactams and Related Heterocycles

Formal Synthesis of (±)‐Trachelanthamidine via Base‐Induced Formal [3+2] Annulation and Intramolecular Cyclization

Enantioselective Synthesis of -Amino Sulfones by aza-Michael Addition to Alkenyl Sulfones

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