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Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium Ions: Application to the Total Synthesis of (±)-epi-Indolizidine 167B and 209D Kiran Indukuri, Jagadish Das and Anil K. Saikia* Department of chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India. Fax:+91 3612690762, e-mail:[email protected] HRMS Spectra List of contents 1. HRMS Spectra of all products S2-S15 S1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is © The Royal Society of Chemistry 2014

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Page 1: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

Supporting Information

Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins

Reaction of Endocyclic N-Acyliminium Ions: Application to the Total

Synthesis of (±)-epi-Indolizidine 167B and 209D

Kiran Indukuri, Jagadish Das and Anil K. Saikia*

Department of chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.

Fax:+91 3612690762, e-mail:[email protected]

HRMS Spectra

List of contents

1. HRMS Spectra of all products S2-S15

S1

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2014

Page 2: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 6a

HRMS of compound 6b

S2

N

O

OTs

H

Page 3: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 6c

HRMS of compound 6d

S3

N

O

OTs

HBr

Page 4: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 6e

HRMS of compound 6g

S4

N

O

OTs

H

Me

N

O

OTs

H

Page 5: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 6h

HRMS of compound 6i

S5

Page 6: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 6j

HRMS of compound 6k

S6

N

O

OTs

HCl

N

O

OTs

H

Page 7: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 6l

HRMS of compound 6m

S7

N

O

OTs

H

Page 8: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 6n

HRMS of compound 6o

S8

N

O

OTs

H

Page 9: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 6d’

HRMS of compound 9p

S9

Page 10: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 9q

HRMS of compound 5p

S10

Page 11: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 5q

HRMS of compound 6p

S11

Page 12: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 6q

HRMS of compound 10p

S12

Page 13: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 10q

HRMS of compound epi-3p

S13

Page 14: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound epi-3q

HRMS of compound 11

S14

Page 15: Supporting Information - Royal Society of Chemistry · Supporting Information Stereoselective Synthesis of O-Tosyl Azabicyclic Derivatives via Aza Prins Reaction of Endocyclic N-Acyliminium

HRMS of compound 12

S15

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